1-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acid → (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

HRID 2046575Notes

Reaction equation

HRID 2046575 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([F:24])[C:5]([C:18]2[N:22]=[C:21]([CH3:23])[O:20][N:19]=2)=[C:6]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[C@@H:13]([NH2:17])[CH2:12][CH2:11]3)[CH:7]=1.[C:25]([O:29][C:30]([NH:32][C:33]1([C:36](O)=[O:37])[CH2:35][CH2:34]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]>>[C:25]([O:29][C:30](=[O:31])[NH:32][C:33]1([C:36](=[O:37])[NH:17][C@@H:13]2[C:14]3[C:10](=[CH:9][C:8]([C:6]4[CH:7]=[C:2]([Cl:1])[CH:3]=[C:4]([F:24])[C:5]=4[C:18]4[N:22]=[C:21]([CH3:23])[O:20][N:19]=4)=[CH:16][CH:15]=3)[CH2:11][CH2:12]2)[CH2:34][CH2:35]1)([CH3:28])([CH3:26])[CH3:27]

Participants

3

Reactant 2

HCID 6883961-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acidHCID 68296736(S)-5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-indan-1-ylamine

Product 1

HCID 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

Procedure

In analogy to the procedures described for the preparation of intermediate A-1 [B], (S)-5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-indan-1-ylamine (intermediate A-11) was coupled with 1-tert-butoxycarbonylamino-cyclopropanecarboxylic acid to yield the title compound as light yellow amorphous solid. MS: 527.2 (MH+, 1Cl).

Sources & evidence

ORD record
ord-f1908105ca78446686bad2acececc35b
Source dataset
uspto-grants-2013_11
Patent number
US08592426B2

Reaction notes

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