Benzenesulfonamide, 3-amino- → 3-(4-{[2-(4-Methoxy-benzylamino)-1-methyl-1H-benzoimidazol-5-yl]-methyl-amino}-pyrimidin-2-ylamino)-benzenesulfonamide hydrochloride

HRID 1391566Notes

Reaction equation

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

Participants

Reactant 2

HCID 7377Benzenesulfonamide, 3-amino-

HCID 59674096HCID 59674096, compound

Product 1

HCID 101290803-(4-{[2-(4-Methoxy-benzylamino)-1-methyl-1H-benzoimidazol-5-yl]-methyl-amino}-pyrimidin-2-ylamino)-benzenesulfonamide hydrochloride

Procedure

The title compound was prepared following the procedure of example one with N5-(2-chloro-pyrimidin-4-yl)-N2-(4-methoxy-benzyl)-1,N5-dimethyl-1H-benzoimidazole-2,5-diamine (82 mg, 0.20 mmol) and 3-amino-benzenesulfonamide (34 mg, 0.20 mmol) as a white solid (83 mg, 72%). 1H NMR (300 MHz, d6-DMSO+NaHCO3) δ10.28 (br s, 2H), 9.53 (br s, 1H), 8.44 (s, 1H), 7.91 (d, J=6.6 Hz, 1H), 7.73 (M, 1H), 7.64 (d, J=8.4 Hz, 1H), 7.43 (d, J=8.4 Hz, 4H), 7.28-7.34 (m, 3H), 6.94 (d, J=8.4 Hz, 2H), 5.81 (m, 1H), 4.67 (d, J=5.7 Hz, 2H), 3.74 (s, 3H), 3.71 (s, 3H), 3.50 (s, 3H). MS (ESI) m/z=545 [M+H]+.

Sources & evidence

ORD record: ord-18793fa58edc422aaf01d74863e41cde
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07338959B2

Reaction notes

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