Diisopropylethylamine → [(S)-1-(7-Bromo-6-methoxy-1-phenyl-1H-benzoimidazol-2-yl)ethyl]-[9-(tetrahydro-pyran-2-yl)-9H-purin-6-yl]amine

HRID 243077Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of (S)-1-(7-bromo-6-methoxy-1-phenyl-1H-benzoimidazol-2-yl)ethylamine dihydrochloride (0.75 g, 1.8 mmol) in IPA (10 mL) was added 6-chloro-9-(tetrahydro-pyran-2-yl)-9H-purine (0.56 mg, 2.34 mmol) and DIPEA (1.2 mL, 7.2 mmol) and the reaction mixture heated at 90° C. for 16 h. The reaction mixture was concentrated in vacuo and the resultant residue subjected to flash chromatography (SiO2, eluting with 0-10% methanol in EtOAc) to give the title compound as a white solid (453 mg, 44%). LCMS (Method C): RT=3.22 min, [M+H]+=548 & 550.

Workup

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

Sources & evidence

ORD record: ord-cdf02f4197d14909ad25f66d9d029c68
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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