Trifluoroacetic acid → 1-Amino-cyclopropanecarboxylic acid {(rac)-5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-7-fluoro-indan-1-yl}-amide

HRID 2046584Notes

Reaction equation

HRID 2046584 reaction equation
C(OC(=O)[NH:7][C:8]1([C:11](=[O:37])[NH:12][CH:13]2[C:21]3[C:16](=[CH:17][C:18]([C:23]4[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([F:30])[C:24]=4[C:31]4[N:35]=[C:34]([CH3:36])[O:33][N:32]=4)=[CH:19][C:20]=3[F:22])[CH2:15][CH2:14]2)[CH2:10][CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O>>[Cl:29][C:27]1[CH:26]=[C:25]([F:30])[C:24]([C:31]2[N:35]=[C:34]([CH3:36])[O:33][N:32]=2)=[C:23]([C:18]2[CH:17]=[C:16]3[C:21](=[C:20]([F:22])[CH:19]=2)[CH:13]([NH:12][C:11]([C:8]2([NH2:7])[CH2:10][CH2:9]2)=[O:37])[CH2:14][CH2:15]3)[CH:28]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 60142707(1-{(Rac)-5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-7-fluoro-indan-1-ylcarbamoyl}-cyclopropyl)-carbamic acid tert-butyl ester

Product 1

HCID 601428331-Amino-cyclopropanecarboxylic acid {(rac)-5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-7-fluoro-indan-1-yl}-amide

Procedure

In analogy to the procedure described for the preparation of intermediate A-11 [C], (1-{(rac)-5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-7-fluoro-indan-1-ylcarbamoyl}-cyclopropyl)-carbamic acid tert-butyl ester (example 31) has been treated with trifluoroacetic acid (90%) to give the title compound as light brown oil. MS: 445.1 (MH+, 1Cl).

Sources & evidence

ORD record
ord-46f1832576114745b80fc85c78acdc1b
Source dataset
uspto-grants-2013_11
Patent number
US08592426B2

Reaction notes

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