Diisopropylethylamine → HCID 68157522, compound

HRID 243067Notes

Reaction equation

Cl.Cl.Cl.Cl.[CH3:5][O:6][C:7]([C:9]1[C:17]2[N:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:15]([C@@H:24]([NH2:26])[CH3:25])=[N:14][C:13]=2[CH:12]=[CH:11][C:10]=1[F:27])=[O:8].Cl[C:29]1[N:37]=[CH:36][N:35]=[C:34]2[C:30]=1[N:31]=[CH:32][N:33]2[CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][O:39]1.CCN(C(C)C)C(C)C>CC(O)C>[CH3:5][O:6][C:7]([C:9]1[C:17]2[N:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:15]([C@@H:24]([NH:26][C:29]3[N:37]=[CH:36][N:35]=[C:34]4[C:30]=3[N:31]=[CH:32][N:33]4[CH:38]3[CH2:43][CH2:42][CH2:41][CH2:40][O:39]3)[CH3:25])=[N:14][C:13]=2[CH:12]=[CH:11][C:10]=1[F:27])=[O:8]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 2-((S)-1-aminoethyl)-5-fluoro-3-phenyl-3H-benzoimidazole-4-carboxylic acid methyl ester dihydrochloride dihydrochloride (1.4 g, 3.8 mmol) in IPA (20 mL) was added 6-chloro-9-(tetrahydro-pyran-2-yl)-9H-purine (1.18 mg, 4.94 mmol) and DIPEA (2.6 mL, 15.2 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 (1.34 g, 67%). LCMS (Method C): RT=3.11 min, [M+H]+=516.

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-b69ac291b11246dd829691b842025904
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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