HCID 69426236, compound → HCID 135445226, compound

HRID 970361Notes

Reaction equation

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

Participants

Conditions

Temperature: 55 °C

Procedure

A solution of 1-(3-chloro-phenyl)-2-[2,6-dimethoxy-5-(4-methyl-6-morpholin-4-yl-1H-benzoimidazol-2-yl)-pyrimidin-4-ylamino]-ethanol (0.041 g, 0.078 mmol) in a mixture of AcOH (17.4 M) and HCl (11.6 M: (1.3 mL: 1.0 mL) was stirred in a sealed tube at 55° C. for 18 hours. Then solvents were evaporated in vacuo and the crude material was purified by preparative HPLC (see method below) to give the title compound as a beige solid (29 mg, 77%), HPLC 99%. LCMS (+ESI, M+H+) m/z 497. IR (KBr, cm−1) 3420, 2961, 2856, 1717, 1635, 1559; 1H NMR (400 MHz DMSO) δ 11.88 (s, 2H), 10.84 (s, 1H), 7.58 (s, 1H), 7.46-7.30 (m, 3H), 6.97 (d, J=2 Hz, 1H), 6.68 (s, 1H), 6.10 (br s, 1H), 4.90 (m, 1H), 3.89 (m, 1H), 3.76 (m, 4H), 3.61 (m, 1H), 3.04 (m, 4H), 2.49 (3H, s); HRMS calcd for C24H25ClN6O4:497.1704; found 497.1698.

Workup

customThen solvents were evaporated in vacuo
customthe crude material was purified by preparative HPLC (see method below)

Sources & evidence

ORD record: ord-975556a5962e4234b81dd66bcf77dd94
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312215B2

Reaction notes

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