4-Amino-N-methylbenzeneethanesulfonamide → HCID 10129155, compound

HRID 1391560Notes

Reaction equation

HRID 1391560 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.[CH3:28][NH:29][S:30]([CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([NH2:41])=[CH:37][CH:36]=1)(=[O:32])=[O:31]>>[ClH:27].[CH3:28][NH:29][S:30]([CH2:33][CH2:34][C:35]1[CH:36]=[CH:37][C:38]([NH:41][C:23]2[N:22]=[C:21]([N:19]([C:17]3[CH:16]=[CH:15][C:12]4[N:13]([CH3:14])[C:9]([NH:8][CH2:1][C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)=[N:10][C:11]=4[CH:18]=3)[CH3:20])[CH:26]=[CH:25][N:24]=2)=[CH:39][CH:40]=1)(=[O:31])=[O:32]

Participants

3

Reactant 2

HCID 134757684-Amino-N-methylbenzeneethanesulfonamideHCID 59674170HCID 59674170, compound

Product 1

HCID 10129155HCID 10129155, compoundYield 33%

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 2-(4-amino-phenyl)-ethanesulfonic acid methylamide (54 mg, 0.25 mmol) to give the desired product as a white solid (49 mg, 33%). 1H NMR (300 MHz, d6-DMSO+NaHCO3) δ 9.97 (br s, 1H), 9.34 (br s, 1H), 7.85 (d, J=6.6 Hz, 1H), 7.49-7.59 (m, 5H), 7.25-7.37 (m, 4H), 7.17 (d, J=8.1 Hz, 3H), 7.03 (q, J=5.4 Hz, 1H), 5.77 (d, J=6.6 Hz, 1H), 4.74 (d, J=5.1 Hz, 2H), 3.72 (s, 3H), 3.46 (s, 3H), 3.21-3.27 (m, 2H), 2.85-2.91 (m, 2H), 2.58 (d, J=4.8 Hz, 3H). MS (ESI) m/z=557 [M+H]+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-aad2731f290a4dd79d071b15776eae15
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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