Ethanamine, 2,2,2-trifluoro- → HCID 53252836, compound

HRID 874376Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:28]([F:31])([F:30])[F:29])[O:13][N:12]=[C:11]([C:14]3[N:15]4[C:19]([C:20]([C:23]([OH:25])=O)=[CH:21][CH:22]=3)=[C:18]([CH3:26])[CH:17]=[C:16]4[CH3:27])[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[F:32][C:33]([F:37])([F:36])[CH2:34][NH2:35]>>[F:32][C:33]([F:37])([F:36])[CH2:34][NH:35][C:23]([C:20]1[C:19]2[N:15]([C:16]([CH3:27])=[CH:17][C:18]=2[CH3:26])[C:14]([C:11]2[CH2:10][C:9]([C:4]3[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=3)([C:28]([F:29])([F:31])[F:30])[O:13][N:12]=2)=[CH:22][CH:21]=1)=[O:25]

Participants

Reactant 2

HCID 9773Ethanamine, 2,2,2-trifluoro-

HCID 58319046HCID 58319046, compound

Product 1

HCID 53252836HCID 53252836, compound

Procedure

Using a procedure similar to that described in Example 1, except using 5-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-1,3-dimethylindolizine-8-carboxylic acid (90 mg) and 2,2,2-trifluoroethylamine (38 mg), the title compound was isolated as a solid (85 mg, 81%). Rf=0.35 (3:7 EA/heptane). MS (ES): M/Z [M+H]=552. 1H NMR (400 MHz, DMSO-d6): 2.18 (s, 3H), 2.19 (s, 3H), 4.11 (qd, J=9.7, 6.6 Hz, 2H), 4.48 (d, J=18.7 Hz, 1H), 4.56 (d, J=18.6 Hz, 1H), 6.57 (s, 1H), 6.62 (d, J=7.0 Hz, 1H), 7.04 (d, J=7.0 Hz, 1H), 7.67 (d, J=1.7 Hz, 2H), 7.84 (t, J=1.9 Hz, 1H), 9.21 (t, J=6.3 Hz, 1H). 19F NMR (376 MHz, DMSO-d6): −78.8 (s, 3F) and −70.6 (t, J=9.9 Hz, 3F)

Sources & evidence

ORD record: ord-faa599c310524961a448d5012f61ed0b
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980893B2

Reaction notes

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