5-Amino-2-methylbenzenesulfonamide → 5-{4-[(2-Benzylamino-1-ethyl-1H-benzoimidazol-5-yl)-methyl-amino]-pyrimidin-2-ylamino}-2-methyl-benzenesulfonamide hydrochloride

HRID 1391580Notes

Reaction equation

HRID 1391580 reaction equation
[CH2:1]([NH:8][C:9]1[N:13]([CH2:14][CH3:15])[C:12]2[CH:16]=[CH:17][C:18]([N:20]([C:22]3[CH:27]=[CH:26][N:25]=[C:24]([Cl:28])[N:23]=3)[CH3:21])=[CH:19][C:11]=2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:29][C:30]1[CH:31]=[CH:32][C:33]([CH3:40])=[C:34]([S:36]([NH2:39])(=[O:38])=[O:37])[CH:35]=1>>[ClH:28].[CH2:1]([NH:8][C:9]1[N:13]([CH2:14][CH3:15])[C:12]2[CH:16]=[CH:17][C:18]([N:20]([CH3:21])[C:22]3[CH:27]=[CH:26][N:25]=[C:24]([NH:29][C:30]4[CH:31]=[CH:32][C:33]([CH3:40])=[C:34]([S:36]([NH2:39])(=[O:37])=[O:38])[CH:35]=4)[N:23]=3)=[CH:19][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 59674155HCID 59674155, compound

Product 1

HCID 101752205-{4-[(2-Benzylamino-1-ethyl-1H-benzoimidazol-5-yl)-methyl-amino]-pyrimidin-2-ylamino}-2-methyl-benzenesulfonamide hydrochloride

Procedure

The title compound was prepared following the procedure of example one with N2-Benzyl-N5-(2-chloro-pyrimidin-4-yl)-1-ethyl-N5-methyl-1H-benzoimidazole-2,5-diamine (98 mg, 0.25 mmol) and 5-amino-2-methyl-benzenesulfonamide (46 mg, 0.25 mmol) as a white solid (83 mg, 58%). 1H NMR (300 MHz, d6-DMSO+NaHCO3) δ 9.54 (s, 1H), 8.56 (s, 1H), 7.80 (d, J=6.3 Hz, 1H), 7.68 (dd, J=8.2 and 1.6 Hz, 1H), 7.15-7.47 (m, 10H), 7.03 (d, J=7.8 Hz, 1H), 5.69 (d, J=6.0 Hz, 1H), 4.68 (d, J=5.7 Hz, 2H), 4.21 (m, 2H), 3.46 (s, 3H), 2.50 (s, 3H), 1.28 (t, J=6.9 Hz, 3H). MS (ESI) m/z=543 [M+H]+.

Sources & evidence

ORD record
ord-cbc82c94a28d46b58272bfcf4558eb7b
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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