Isopropylamine → Trifluoroacetic acid

HRID 713228Notes

Reaction equation

[CH3:1][CH:2]([NH2:4])[CH3:3].[OH:5][C:6]([C:8]([F:11])([F:10])[F:9])=[O:7].[CH2:12]([N:19]1[CH2:28][CH2:27][C:26]2[C:21](=[N:22][C:23](Cl)=[C:24]([N:29]3[CH2:34][CH2:33][CH:32]([C:35]([C:37]4[CH:42]=[C:41]([Cl:43])[CH:40]=[CH:39][C:38]=4[F:44])=[O:36])[CH2:31][CH2:30]3)[N:25]=2)[CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[CH2:12]([N:19]1[CH2:28][CH2:27][C:26]2[C:21](=[N:22][C:23]([NH:4][CH:2]([CH3:3])[CH3:1])=[C:24]([N:29]3[CH2:34][CH2:33][CH:32]([C:35]([C:37]4[CH:42]=[C:41]([Cl:43])[CH:40]=[CH:39][C:38]=4[F:44])=[O:36])[CH2:31][CH2:30]3)[N:25]=2)[CH2:20]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1.[C:6]([OH:7])([C:8]([F:11])([F:10])[F:9])=[O:5]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of propan-2-amine (31.5 μL, 0.366 mmol), (1-(6-benzyl-3-chloro-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-2-yl)piperidin-4-yl)(5-chloro-2-fluorophenyl)methanone TFA salt (112.4 mg, 0.183 mmol), sodium tert-butoxide (35.2 mg, 0.366 mmol), BINAP (17.1 mg, 0.027 mmol) and Pd2(dba)3 (8.4 mg, 9.16 μmol) in toluene (611 μL) was heated at 100° C. for 16 h. The mixture was purified by HPLC Method A to afford (1-(6-benzyl-3-(isopropylamino)-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-2-yl)piperidin-4-yl)(5-chloro-2-fluorophenyl)methanone as its TFA salt (41.7 mg, 35.8%) as a yellow film. ESI-MS m/z [M+H]+ 522.4.

Workup

customThe mixture was purified by HPLC Method A

Sources & evidence

ORD record: ord-0457c549130d43399dd2e5714a0f6eba
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181249B2

Reaction notes

Loading…