2,5-Difluoro-4-nitrobenzoic acid → HCID 57991873, compound

HRID 2075319Notes

Reaction equation

HRID 2075319 reaction equation
[NH2:1][C@@H:2]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=1)[CH2:3][NH:4][C:5]1[S:6][C:7]([C:10]2[CH:15]=[C:14](F)[C:13]([N+:17]([O-])=O)=[CH:12][C:11]=2[F:20])=[N:8][N:9]=1.FC1C=C([N+]([O-])=O)C(F)=C[C:34]=1[C:43](O)=[O:44]>>[NH2:1][C@@H:2]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:30])([F:31])[F:29])=[CH:24][CH:23]=1)[CH2:3][NH:4][C:5]1[S:6][C:7]([C:10]2[CH:15]=[C:14]3[C:13](=[CH:12][C:11]=2[F:20])[NH:17][C:43](=[O:44])[CH2:34]3)=[N:8][N:9]=1

Participants

3

Reactant 2

HCID 2463752,5-Difluoro-4-nitrobenzoic acid2×HCID 67089501HCID 67089501, compound

Product 1

HCID 57991873HCID 57991873, compound

Procedure

The title compound was prepared according to the procedure described for Example 2 starting with N—((S)-2-amino-3-(4-(trifluoromethyl)phenyl)propyl)-5-(2,5-difluoro-4-nitrophenyl)-1,3,4-thiadiazol-2-amine, which was prepared in a similar manner as shown in Scheme 1 with 2,5-difluoro-4-nitrobenzenecarboxylic acid as the starting material. 2,5-Difluoro-4-nitrobenzenecarboxylic acid was purchased from Ryan Scientific Inc. LCMS (API-ES) m/z (%): 452.5 (100%, M++H); 1H NMR (400 MHz, CD3OD): δ ppm 3.13-3.26 (m, 2H), 3.62-3.71 (m, 3H), 3.78-3.84 (m, 1H), 3.85-4.10 (m, 1H), 3.99 (d, J=2.35 Hz, 4H), 6.83-6.89 (m, 1H), 7.61 (d, J=8.02 Hz, 2H), 7.75 (d, J=8.02 Hz, 2H), 7.99 (d, J=6.85 Hz, 1H).

Workup

  1. customwas prepared in a similar manner

Sources & evidence

ORD record
ord-4ed19045d7ba4e139dfe2e3a76d42e18
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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