Hydrochloric Acid → HCID 69265372, compound

HRID 1391554Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of N5-(2-chloropyrimidin-4-yl)-N2-isopropyl-N5,1-dimethyl-1H-benzimidazole-2,5-diamine (83 mg, 0.25 mmol) and 1-(4-aminophenyl)methane-sulfonamide (47 mg, 0.25 mmol) in ethanol (2.5 ml) was added a solution of HCl (0.25 ml, 1M in diethyl ether) and the reaction was heated to 70° C. After 20 hours, the reaction mixture was neutralized with the addition of solid NaHCO3. The mixture was filtered and the filtrate was purified with silica gel to give the title compound as a white solid. 1H NMR (300 MHz, d6-DMSO) δ 9.16 (s, 1H), 7.78 (m, 3H), 7.19 (d, J=8.1 Hz, 3H), 7.09 (d, J=1.8 Hz, 1H), 6.82 (dd, J=8.1 and 1.8 Hz, 1H), 6.75 (s, 2H), 6.49 (d, J=7.8 Hz, 1H), 5.62 (d, J=6.0 Hz, 1H), 4.15 (s, 2H), 4.02 (m, 1H), 3.51 (s, 3H), 3.44 (s, 3H), 1.24 (d, J=6.6 Hz, 6H) ppm. MS (ESI) m/z=481 [M+H]+.

Workup

filtrationThe mixture was filtered
customthe filtrate was purified with silica gel

Sources & evidence

ORD record: ord-aa6c6c2db4514eb293e678b1595e7a9d
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07338959B2

Reaction notes

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