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

HRID 2046576Notes

Reaction equation

HRID 2046576 reaction equation
C(OC(=O)[NH:7][C:8]1([C:11](=[O:36])[NH:12][C@@H:13]2[C:21]3[C:16](=[CH:17][C:18]([C:22]4[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([F:29])[C:23]=4[C:30]4[N:34]=[C:33]([CH3:35])[O:32][N:31]=4)=[CH:19][CH:20]=3)[CH2:15][CH2:14]2)[CH2:10][CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:28][C:26]1[CH:25]=[C:24]([F:29])[C:23]([C:30]2[N:34]=[C:33]([CH3:35])[O:32][N:31]=2)=[C:22]([C:18]2[CH:17]=[C:16]3[C:21](=[CH:20][CH:19]=2)[C@@H:13]([NH:12][C:11]([C:8]2([NH2:7])[CH2:9][CH2:10]2)=[O:36])[CH2:14][CH2:15]3)[CH:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 60142568(1-{(S)-5-[5-Chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-indan-1-ylcarbamoyl}-cyclopropyl)-carbamic acid tert-butyl ester

Product 1

HCID 601425691-Amino-cyclopropanecarboxylic acid{(S)-5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-indan-1-yl}-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In analogy to the procedure described for the preparation of intermediate A-11 [C], (1-{(S)-5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-indan-1-ylcarbamoyl}-cyclopropyl)-carbamic acid tert-butyl ester (example 23) was treated with trifluoro-acetic acid (90%) in CH2Cl2 to yield the title compound light yellow amorphous solid. MS: 427.1 (MH+, 1Cl).

Sources & evidence

ORD record
ord-62c7f1d6dd2b461a9a5cae0d0d8c5be2
Source dataset
uspto-grants-2013_11
Patent number
US08592426B2

Reaction notes

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