Diisopropylethylamine → HCID 68157695, compound

HRID 243072Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of (R)-1-(6,7-difluoro-1-phenyl-1H-benzoimidazol-2-yl)-2-methoxyethylamine dihydrochloride (0.20 g, 0.68 mmol) in 2-butanol (5 mL) was added 6-chloro-9-(tetrahydro-pyran-2-yl)-9H-purine (0.195 mg, 0.81 mmol) and DIPEA (233 μL, 1.36 mmol) and the reaction mixture heated at 90° C. for 16 h. The reaction mixture was concentrated in vacuo and the resultant residue was subjected to flash chromatography (SiO2, eluting with 0-10% methanol in EtOAc) to give the title compound as an off white solid (290 mg, 84%). LCMS (Method C): RT=3.48 min, [M+H]+=506.

Workup

concentrationThe reaction mixture was concentrated in vacuo
washthe resultant residue was subjected to flash chromatography (SiO2, eluting with 0-10% methanol in EtOAc)

Sources & evidence

ORD record: ord-9534bfea5dcc41e2b0d668372cd67525
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

Loading…