2,2,2-Trifluoroethylamine hydrochloride → HCID 89782000, compound

HRID 1056390Notes

Reaction equation

[NH2:1][C:2]1[C:10]([Br:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl.[F:13][C:14]([F:18])([F:17])[CH2:15][NH2:16].CCN(C(C)C)C(C)C>>[NH2:1][C:2]1[C:10]([Br:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:16][CH2:15][C:14]([F:18])([F:17])[F:13])=[O:6]

Participants

Reactant 3

HCID 97722,2,2-Trifluoroethylamine hydrochloride

HCID 81531Diisopropylethylamine

HCID 2702592-Amino-3-bromobenzoic acid

Product 1

HCID 89782000HCID 89782000, compoundYield 81%

Procedure

2-Amino-3-bromo-N-(2,2,2-trifluoroethyl)benzamide (501a) (1.67 g, 81%) was prepared according to the procedures described for 720 using (2-amino-3-bromo-benzoic acid (1.5 g, 6.94 mmol, Sigma Aldrich), 2,2,2-trifluoroethylamine hydrochloride (1.1 g, 8.33 mmol, TCI), and DIEA (2.9 mL, 16.66 mmol, Sigma Aldrich) as the reagents. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.00 (1H, t, J=6.16 Hz) 7.52-7.63 (2H, m) 6.57 (1H, t, J=7.82 Hz) 6.48 (1H, s) 4.05 (2H, qd, J=9.75, 6.36 Hz). m/z (ESI, +ve) 298.9/300.9 (M+H)+.

Sources & evidence

ORD record: ord-05c70b6f676940889761029ac9b1aaf6
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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