Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [OH-:1].[Na+].OO.[C:5]([C:7]1([NH:27][C:28](=O)[CH3:29])[CH2:12][CH2:11][CH:10]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH3:25])=[C:19]([CH3:26])[CH:18]=2)(=[O:16])=[O:15])[CH2:9][CH2:8]1)#[N:6]>C(O)C.O>[CH2:24]([O:23][C:20]1[CH:21]=[CH:22][C:17]([S:14]([NH:13][CH:10]2[CH2:9][CH2:8][C:7]3([N:27]=[C:28]([CH3:29])[NH:6][C:5]3=[O:1])[CH2:12][CH2:11]2)(=[O:15])=[O:16])=[CH:18][C:19]=1[CH3:26])[CH3:25]
Reactant: [OH-]
Reactant: CCOc1ccc(S(=O)(=O)NC2CCC(C#N)(NC(C)=O)CC2)cc1C
Agent: OO
Agent: [Na+]
Solvent: CCO
Solvent: O
Product: CCOc1ccc(S(=O)(=O)NC2CCC3(CC2)N=C(C)NC3=O)cc1C
Temperature: 80 °C
Yield: 48.3 %

Procedure:
5N Sodium hydroxide (320 ul, 1.59 mmol) followed by 50% aqueous hydrogen peroxide (157 ul, 2.55 mmol) were added to solution of N-(1-cyano-4-(4-ethoxy-3-methylphenylsulfonamido)cyclohexyl)acetamide (Intermediate 126, 242 mg, 0.638 mmol) in ethanol (6.4 ml). The reaction was heated to 80° C. for three hours. LCMS indicated approximately 3:1 product:starting material by co-injection. The reaction was diluted with water and extract with four volumes ethyl acetate. The combined organics were dried over sodium sulfate, filtered and concentrate to 226 mg crude. TLC (10% methanol in ethyl acetate): Rf starting material 0.66; major spot Rf=0.25. The crude was chromatographed on Biotage 12M eluting 0-100% ethyl acetate in (10% methanol in ethyl acetate) to give the product as an off-white solid (117 mg, 0.308 mmol). LCMS [M+H]=380.2.
Reaction SMILES: Br[C:2]1[C:15]([CH3:16])=[CH:14][C:5]([O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])=[CH:4][C:3]=1[CH3:17].CCCCCC.C([Li])CCC.[B:29](OC(C)C)([O:34]C(C)C)[O:30]C(C)C.Cl>O1CCCC1>[Si:7]([O:6][C:5]1[CH:14]=[C:15]([CH3:16])[C:2]([B:29]([OH:34])[OH:30])=[C:3]([CH3:17])[CH:4]=1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]
Reactant: CC(C)OB(OC(C)C)OC(C)C
Reactant: Cc1cc(O[Si](C)(C)C(C)(C)C)cc(C)c1Br
Agent: Cl
Agent: [Li]CCCC
Solvent: C1CCOC1
Solvent: CCCCCC
Product: Cc1cc(O[Si](C)(C)C(C)(C)C)cc(C)c1B(O)O
Temperature: -78 °C
Yield: 53.5 %

Procedure:
To a solution (250 mL) of (4-bromo-3,5-dimethylphenoxy)(tert-butyl)dimethylsilane (39.2 g, 124 mmol) in tetrahydrofuran was added n-butyllithium hexane solution (1.6 M, 90.0 mL, 144 mmol) under stirring at −78° C. The reaction mixture was stirred at the same temperature for 2 hr, and triisopropyl borate (40.0 mL, 173 mmol) was added. The mixture was allowed to warm to room temperature and stirred for 3 hr. To the reaction mixture was added 2 M hydrochloric acid (180 mL), and the mixture was stirred for 6 hr. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=1/4) to give the title compound (18.6 g, yield 53%) as pale-yellow prism crystals.
Reaction SMILES: [O:1]=[C:2]1[N:7]([CH2:8][C:9]#[CH:10])[N:6]=[N:5][C:4]2=[C:11]([C:14](=[S:16])[NH2:15])[N:12]=[CH:13][N:3]12.Br[CH2:18][C:19]([C:21]1[S:22][CH:23]=[CH:24][N:25]=1)=O.C(N(CC)CC)C>CC#N>[S:22]1[CH:23]=[CH:24][N:25]=[C:21]1[C:19]1[N:15]=[C:14]([C:11]2[N:12]=[CH:13][N:3]3[C:2](=[O:1])[N:7]([CH2:8][C:9]#[CH:10])[N:6]=[N:5][C:4]=23)[S:16][CH:18]=1
Reactant: O=C(CBr)c1nccs1
Reactant: C#CCn1nnc2c(C(N)=S)ncn2c1=O
Solvent: CCN(CC)CC
Solvent: CC#N
Product: C#CCn1nnc2c(-c3nc(-c4nccs4)cs3)ncn2c1=O
Yield: 38 %

Procedure:
4-oxo-3-(prop-2-ynyl)-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carbothioamide (0.43 mmol) and 2-bromo-1-(1,3-thiazol-2-yl)ethanone (0.43 mmol) were stirred in MeCN (2 mL) overnight at room temperature. The reaction mixture containing a newly formed precipitate was then treated with sufficient triethylamine to solubilise before evaporating to dryness and purifying by column chromatography, eluting with 10% MeCN/DCM, to give the title compound. Yield 38%. δH (DMSO-d6) 9.00 (1H, s) 8.44 (1H, s), 7.97 (1H, d, J=3.2), 7.85 (1H, d, J=2.8), 5.16 (2H, d, J=2.4), 3.55 (1H, t, J=2.4).