5-Amino-2-methylbenzenesulfonamide → HCID 10218748, compound

HRID 1391607Notes

Reaction equation

C(OC(=O)[N:7]([C:27]1[CH:32]=[CH:31][C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:29][CH:28]=1)[C:8]1[N:12]([CH3:13])[C:11]2[CH:14]=[CH:15][C:16]([N:18]([C:20]3[CH:25]=[CH:24][N:23]=[C:22]([Cl:26])[N:21]=3)[CH3:19])=[CH:17][C:10]=2[N:9]=1)(C)(C)C.[NH2:38][C:39]1[CH:40]=[CH:41][C:42]([CH3:49])=[C:43]([S:45]([NH2:48])(=[O:47])=[O:46])[CH:44]=1>>[ClH:26].[C:33]([C:30]1[CH:31]=[CH:32][C:27]([NH:7][C:8]2[N:12]([CH3:13])[C:11]3[CH:14]=[CH:15][C:16]([N:18]([CH3:19])[C:20]4[CH:25]=[CH:24][N:23]=[C:22]([NH:38][C:39]5[CH:40]=[CH:41][C:42]([CH3:49])=[C:43]([S:45]([NH2:48])(=[O:46])=[O:47])[CH:44]=5)[N:21]=4)=[CH:17][C:10]=3[N:9]=2)=[CH:28][CH:29]=1)([CH3:36])([CH3:34])[CH3:35]

Participants

Reactant 2

HCID 2355115-Amino-2-methylbenzenesulfonamide

HCID 59674158HCID 59674158, compound

Product 1

HCID 10218748HCID 10218748, compoundYield 54.4%

Procedure

The title compound was prepared following the procedure of example 5 using (4-tert-Butyl-phenyl)-{5-[(2-chloro-pyrimidin-4-yl)-methyl-amino]-1-methyl-1H-benzoimidazol-2-yl}-carbamic acid tert-butyl ester (104 mg, 0.20 mmol) and 5-amino-2-methyl-benzenesulfonamide (37 mg, 0.20 mmol) to give the desired product as a white solid (66 mg, 48%). 1H NMR (300 MHz, d6-DMSO+NaHCO3) δ 9.35 (s, 1H), 8.96 (s, 1H), 8.62 (s, 1H), 7.71-7.78 (m, 4H), 7.32-7.38 (M, 3H), 7.27 (s, 1H), 7.17-7.23 (M, 3H), 6.96 (d, J=8.4 Hz, 1H), 5.63 (d, J=6.0 Hz, 1H), 3.74 (s, 3H), 3.48 (s, 3H), 2.50 (s, 3H), 1.28 (s, 9H). MS (ESI) m/z=571 [M+H]+.

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-6a16181959ce4d999aa67db9f8015369
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07338959B2

Reaction notes

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