Diisopropylethylamine → HCID 71516589, compound

HRID 632719Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

In a microwave vial containing 1-[2-chloro-2-(4-trifluoromethyl-phenyl)-ethyl]-azetidine (32.26 mg; 0.12 mmol; 1.00 eq.) from last step in acetonitrile (2.00 ml) was added 5-(4-fluoro-phenyl)-6-piperazin-1-yl-pyrimidin-4-ylamine (33.43 mg; 0.12 mmol; 1.00 eq.), followed by DIPEA (0.06 ml; 0.37 mmol; 3.00 eq.). The clear solution was stirred at 60° C. overnight and then 75° C. for 3 h before the mixture was concentrated and purified with waters pre-HPLC. LC-MS: (M+1=501, obsd.=501)

Workup

concentration75° C. for 3 h before the mixture was concentrated
custompurified with waters pre-HPLC

Sources & evidence

ORD record: ord-f5ff3e5395bd4e448451a9edc06f49a2
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321760B2

Reaction notes

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