Cyclohexanecarboxaldehyde → 3-Cyclohexyl-7-(2',4'-dimethoxyphenyl)-1,2,3,4-tetrahydro-1,2,4-benzothiadiazine-1,1-dioxide

HRID 496111Notes

Reaction equation

HRID 496111 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH2:13])=[C:7]([S:9]([NH2:12])(=[O:11])=[O:10])[CH:8]=1)#N.[CH3:14][O:15][C:16]1[CH:21]=[C:20]([O:22][CH3:23])C=[CH:18][C:17]=1B(O)O.[CH:27]1([CH:33]=O)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>>[CH:27]1([CH:33]2[NH:13][C:6]3[CH:5]=[CH:4][C:3]([C:1]4[CH:18]=[CH:17][C:16]([O:15][CH3:14])=[CH:21][C:20]=4[O:22][CH3:23])=[CH:8][C:7]=3[S:9](=[O:11])(=[O:10])[NH:12]2)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

4

Reactant 3

HCID 16275CyclohexanecarboxaldehydeHCID 27343412,4-Dimethoxybenzeneboronic acidHCID 223239942-Amino-5-cyanobenzene-1-sulfonamide2×

Product 1

HCID 223240113-Cyclohexyl-7-(2',4'-dimethoxyphenyl)-1,2,3,4-tetrahydro-1,2,4-benzothiadiazine-1,1-dioxide

Procedure

5-Iodo-2-aminobenzenesulfonamide (see compound 37) was transformed by Method H (using 2,4-dimethoxyphenylboronic acid) and Method G (using cyclohexanecarboxaldehyde). M.p. 208-213° C.

Sources & evidence

ORD record
ord-7e61584f73cd46e7b8b01026a9116a86
Source dataset
uspto-grants-2005_09
Patent number
US06943159B1

Reaction notes

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