5-Amino-2-methylbenzenesulfonamide → HCID 10175108, compound

HRID 1391558Notes

Reaction equation

HRID 1391558 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:30]=[CH:31][C:32]([CH3:39])=[C:33]([S:35]([NH2:38])(=[O:37])=[O:36])[CH:34]=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:30]=[CH:31][C:32]([CH3:39])=[C:33]([S:35]([NH2:38])(=[O:36])=[O:37])[CH:34]=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 2355115-Amino-2-methylbenzenesulfonamideHCID 59674170HCID 59674170, compound

Product 1

HCID 10175108HCID 10175108, compoundYield 81%

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 5-amino-2-methyl-benzenesulfonamide (47 mg, 0.25 mmol) to give the desired product as a pink solid (114 mg, 81%). 1H NMR (300 MHz, d6-DMSO+NaHCO3) δ 10.31 (br s, 2H), 9.61 (br s, 1H), 8.46 (s, 1H), 7.88 (d, J=6.6 Hz, 1H), 7.63 (m, 2H), 7.51 (d, J=7.5 Hz, 2H), 7.23-7.39 (m, 7H), 5.77 (d, J=6.3 Hz, 1H), 4.77 (d, H=6.0 Hz, 2H), 3.74 (s, 3H), 3.50 (s, 3H), 2.52 (s, 3H). MS (ESI) m/z=529 [M+H]+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-7c45bf800c4f462fad3d05b2dc865eab
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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