2,3,4-Trifluorobenzoic acid → HCID 12135111, compound

HRID 1835660Notes

Reaction equation

HRID 1835660 reaction equation
F[C:2]1[C:10]([F:11])=[C:9]([F:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH2:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([NH:20][CH3:21])=[O:19])=[CH:16][C:15]=1[F:24].[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[F:11][C:10]1[C:2]([NH:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([NH:20][CH3:21])=[O:19])=[CH:16][C:15]=2[F:24])=[C:3]([CH:7]=[CH:8][C:9]=1[F:12])[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 3029322,3,4-Trifluorobenzoic acidHCID 2733832Lithium HexamethyldisilazideHCID 132499104-amino-3-fluoro-N-methylbenzamide

Product 1

HCID 12135111HCID 12135111, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,3,4-Trifluorobenzoic acid and 4-amino-3-fluoro-N-methylbenzamide [Anker et al, Helv. Chim. Acta., 67(3), 706-716 (1984)] were reacted in the presence of LiHMDS solution in THF by the general procedure of Example 1, Step B. After workup, followed by purification by chromatography on silica gel (100% EtOAc as eluant), 3,4-difluoro-2-{2-fluoro-4-[(methylamino)carbonyl]anilino}-benzoic acid was isolated as a pale, yellow-orange solid; m.p. (EtOAc/MeOH) 242-244° C. 1H NMR [400 MHz, (CD3)2SO] δ 13.70 (v br s, 1 H), 9.28 (br s, 1 H), 8.36 (br d, J=4.5 Hz, 1 H), 7.88-7.80 (m, 1 H) 7.69 (dd, J=12.5, 1.7 Hz, 1 H), 7.60 (dd, J=8.5, 1.5 Hz, 1 H), 7.19 (dd, J=16.7, 9.3 Hz, 1 H), 7.01 (ddd, J=8.6, 8.6, 5.8 Hz, 1 H), 2.77 (d, J=4.4 Hz, 3 H). Anal. calcd. for C15H11F3N2O3: C, 55.6; H, 3.4; N, 8.6. Await Found.

Workup

  1. customAfter workup, followed by purification by chromatography on silica gel (100% EtOAc as eluant)

Sources & evidence

ORD record
ord-ca516dea8700407bb94389d81c5cb2d7
Source dataset
uspto-grants-2004_08
Patent number
US06770778B2

Reaction notes

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