Trifluoroacetic acid → 1-Amino-cyclopropanecarboxylic acid {(rac)-6-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-2,3-dihydro-benzofuran-3-yl}-amide

HRID 2046594Notes

Reaction equation

C(OC(=O)[NH:7][C:8]1([C:11](=[O:36])[NH:12][CH:13]2[C:17]3[CH:18]=[CH:19][C:20]([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:21][C:16]=3[O:15][CH2:14]2)[CH2:10][CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O>>[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:20]2[CH:19]=[CH:18][C:17]3[CH:13]([NH:12][C:11]([C:8]4([NH2:7])[CH2:10][CH2:9]4)=[O:36])[CH2:14][O:15][C:16]=3[CH:21]=2)[CH:27]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 60143097(1-{(Rac)-6-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-2,3-dihydro-benzofuran-3-ylcarbamoyl}-cyclopropyl)-carbamic acid tert-butyl ester

Product 1

HCID 601430981-Amino-cyclopropanecarboxylic acid {(rac)-6-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-2,3-dihydro-benzofuran-3-yl}-amide

Procedure

In analogy to the procedure described for the preparation of intermediate A-11 [C], (1-{(rac)-6-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-2,3-dihydro-benzofuran-3-ylcarbamoyl}-cyclopropyl)-carbamic acid tert-butyl ester (example 44) has been treated with trifluoroacetic acid (90%) to give the title compound as light yellow oil. MS: 429.1 (MH+, 1Cl).

Sources & evidence

ORD record: ord-f75b4f2df0bc40dda49c7831b2b5cc8e
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592426B2

Reaction notes

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