Diisopropylethylamine → HCID 44622552, compound

HRID 42334Notes

Reaction equation

Cl[C:2]1[N:3]=[C:4]([NH:19][CH2:20][C:21]([F:24])([F:23])[F:22])[C:5]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1.[N:25]1([C:30]2[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=2)[CH2:33][NH2:34])[CH:29]=[N:28][CH:27]=[N:26]1.C(N(C(C)C)CC)(C)C.O.C(#N)C>CN1C(=O)CCC1>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[CH:9]=[CH:8][C:6]3[N:7]=[C:2]([NH:34][CH2:33][C:32]4[CH:35]=[CH:36][CH:37]=[C:30]([N:25]5[CH:29]=[N:28][CH:27]=[N:26]5)[CH:31]=4)[N:3]=[C:4]([NH:19][CH2:20][C:21]([F:24])([F:23])[F:22])[C:5]=3[N:11]=2)=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of [2-Chloro-6-(4-fluoro-phenyl)-pyrido[3,2-d]pyrimidin-4-yl]-(2,2,2-trifluoro-ethyl)-amine (108 mg) and 3-[1,2,4]Triazol-1-yl-benzylamine (124 mg) was dissolved in NMP (1.9 mL) and treated with diisopropylethylamine (0.060 mL). The reaction mixture was sealed and heated by microwave to 160° C. for 1 h. After cooling, the reaction mixture was added dropwise to a stirred solution of water:acetonitrile (1:1). The resulting precipitate was filtered and purified by silica gel chromatography (0-10% EtOH (containing 11% NH4OH sat aq):DCM) to afford 89 mg (60% yield) of the title compound, which was characterized by its NMR and mass spectrum as follows: 1H NMR (d6-DMSO): d 4.29-4.41 (m, 2H), 4.63-4.66 (m, 2H), 7.29-7.35 (m, 2H), 7.40-7.51 (m, 2H), 7.70-7.75 (m, 3H), 7.87 (s, 1H), 8.19-8.22 (m, 2H), 8.36-8.39 (m, 2H), 8.61-8.64 (m, 1H), 9.25 (s, 1H); MS (m/z): 495.3 ([M+H]+, 100).

Workup

customThe reaction mixture was sealed
temperatureAfter cooling
filtrationThe resulting precipitate was filtered
custompurified by silica gel chromatography (0-10% EtOH (containing 11% NH4OH sat aq):DCM)

Sources & evidence

ORD record: ord-8533b667cfd5417489b8eee5a1042374
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536187B2

Reaction notes

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