2,2,2-trifluoro-N-methylethanamine → HCID 67298046, compound

HRID 1520360Notes

Reaction equation

HRID 1520360 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]([N:22](C)[CH2:23][C:24]([F:27])([F:26])[F:25])=[O:21])[CH:18]=3)[N:13]=[C:12]([C:29]3[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=3)[N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8].FC(F)(F)CNC>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]([NH:22][CH2:23][C:24]([F:27])([F:25])[F:26])=[O:21])[CH:18]=3)[N:13]=[C:12]([C:29]3[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=3)[N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

3

Reactant 2

HCID 5203012,2,2-trifluoro-N-methylethanamineHCID 67297980HCID 67297980, compound

Product 1

HCID 67298046HCID 67298046, compound

Procedure

4-(3-chloro-4-fluorophenylamino)-2-(pyridin-3-yl)-N-(2,2,2-trifluoroethyl)quinazoline-6-carboxamide was synthesized in a similar manner to that described for 4-(3-chloro-4-fluorophenylamino)-N-methyl-2-(pyridin-3-yl)-N-(2,2,2-trifluoroethyl)quinazoline-6-carboxamide substituting 2,2,2-trifluoroethylamine for 2,2,2-trifluoro-N-methylethylamine. The resulting product was analyzed. LCMS: r.t=1.934 min, [M+1]+=476.0. 1H-NMR (400 MHz, DMSO-d6): δ 10.43 (s, 1H), 9.54 (s, 1H), 9.32 (t, J=6.1 Hz, 1H), 9.14 (s, 1H), 8.72 (d, J=4.6 Hz, 1H), 8.68 (d, J=8.0 Hz, 1H), 8.32 (d, J=8.7 Hz, 1H), 8.27 (dd, J=6.7, 2.2 Hz, 1H), 7.98 (d, J=8.7 Hz, 1H), 7.96-7.90 (m, 1H), 7.62-7.51 (m, 2H), 4.27-4.14 (m, 2H).

Workup

  1. customr.t=1.934 min, [M+1]+=476.0

Sources & evidence

ORD record
ord-082a30a7e22d46cc819563776de5027f
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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