Diisopropylethylamine → [6-(5-Chloro-pyridin-2-yl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-yl]-[(S)-cyclopropyl-(6-trifluoromethyl-pyridin-3-yl)-methyl]-amine

HRID 241878Notes

Reaction equation

Cl.Cl.[CH:3]1([C@@H:6]([C:8]2[CH:9]=[N:10][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:13]=2)[NH2:7])[CH2:5][CH2:4]1.C(N(CC)C(C)C)(C)C.Br[C:28]1[C:29]2[CH2:37][N:36]([C:38]3[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][N:39]=3)[CH2:35][CH2:34][C:30]=2[N:31]=[CH:32][N:33]=1>C(#N)C>[Cl:44][C:41]1[CH:42]=[CH:43][C:38]([N:36]2[CH2:35][CH2:34][C:30]3[N:31]=[CH:32][N:33]=[C:28]([NH:7][C@@H:6]([CH:3]4[CH2:5][CH2:4]4)[C:8]4[CH:9]=[N:10][C:11]([C:14]([F:17])([F:15])[F:16])=[CH:12][CH:13]=4)[C:29]=3[CH2:37]2)=[N:39][CH:40]=1

Participants

Conditions

Temperature: 180 °C

Procedure

To a stirred solution of (S)-cyclopropyl(6-(trifluoromethyl)pyridin-3-yl)methanamine dihydrochloride (0.048 g, 0.17 mmol) and N,N-diisopropylethylamine (96 uL, 0.55 mmol) in acetonitrile (1.8 mL) was added 4-bromo-6-(5-chloropyridin-2-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (0.045 g, 0.14 mmol). The reaction was heated in microwave for 7 hours at 180° C. The mixture was concentrated and the residue was purified by silica gel column followed by semi-prep HPLC to obtain 7.8 mg of white solid.

Workup

concentrationThe mixture was concentrated
customthe residue was purified by silica gel column

Sources & evidence

ORD record: ord-edc55f4eb84747b4bfefa912a5aa58cb
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653091B2

Reaction notes

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