1-(4-Aminophenyl)methanesulfonamide → HCID 10153034, compound

HRID 1391559Notes

Reaction equation

HRID 1391559 reaction equation
[CH2:1]([NH:8][C:9]1[N:13]([CH3:14])[C:12]2[CH:15]=[CH:16][C:17]([N:19]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([Cl:27])[N:22]=3)[CH3:20])=[CH:18][C:11]=2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][S:36]([NH2:39])(=[O:38])=[O:37])=[CH:31][CH:30]=1>>[ClH:27].[CH2:1]([NH:8][C:9]1[N:13]([CH3:14])[C:12]2[CH:15]=[CH:16][C:17]([N:19]([CH3:20])[C:21]3[CH:26]=[CH:25][N:24]=[C:23]([NH:28][C:29]4[CH:34]=[CH:33][C:32]([CH2:35][S:36]([NH2:39])(=[O:37])=[O:38])=[CH:31][CH:30]=4)[N:22]=3)=[CH:18][C:11]=2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 108214071-(4-Aminophenyl)methanesulfonamideHCID 59674170HCID 59674170, compound

Product 1

HCID 10153034HCID 10153034, compoundYield 60.2%

Procedure

The title compound was prepared following the procedure of Example 1 with N2-benzyl-N5-(2-chloropyrimidin-4-yl)-N5,1-dimethyl-1H-benzimidazole-2,5-diamine (95 mg, 0.25 mmol) and (4-amino-phenyl)-methanesulfonamide (46 mg, 0.25 mmol) to give the desired product as a white solid (85 mg, 60%). 1H NMR (300 MHz, d6-DMSO+NaHCO3) δ 10.17 (brs, 2H), 9.53 (brs, 1H), 7.90 (d, J=6.6 Hz, 1H), 7.61 (d, J=8.4 Hz, 3H), 7.51 (d, J=7.5 Hz, 2H), 7.22-7.39 (m, 6H), 6.82 (s, 2H), 5.87 (d, J=6.0 Hz, 1H), 4.76 (d, J=5.7 Hz, 2H), 4.19 (s, 2H), 3.74 (s, 3H) 3.49 (s, 3H). MS (ESI) m/z=529 [M+H]+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-ca937058d9384c8da1452bdf3d878afe
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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