1,2-Oxazole-5-carboxylic acid → Isoxazole-5-carboxylic acid (3-{(S)-5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-indan-1-ylcarbamoyl}-oxetan-3-yl)-amide

HRID 2046600Notes

Reaction equation

HRID 2046600 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([F:31])[C:5]([C:25]2[N:29]=[C:28]([CH3:30])[O:27][N:26]=2)=[C:6]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[C@@H:13]([NH:17][C:18]([C:20]2([NH2:24])[CH2:23][O:22][CH2:21]2)=[O:19])[CH2:12][CH2:11]3)[CH:7]=1.[O:32]1[C:36]([C:37](O)=[O:38])=[CH:35][CH:34]=[N:33]1>>[Cl:1][C:2]1[CH:3]=[C:4]([F:31])[C:5]([C:25]2[N:29]=[C:28]([CH3:30])[O:27][N:26]=2)=[C:6]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[C@@H:13]([NH:17][C:18]([C:20]2([NH:24][C:37]([C:36]4[O:32][N:33]=[CH:34][CH:35]=4)=[O:38])[CH2:21][O:22][CH2:23]2)=[O:19])[CH2:12][CH2:11]3)[CH:7]=1

Participants

3

Reactant 2

HCID 20605991,2-Oxazole-5-carboxylic acidHCID 601410403-Amino-oxetane-3-carboxylic acid {(S)-5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-indan-1-yl}-amide

Product 1

HCID 60141042Isoxazole-5-carboxylic acid (3-{(S)-5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-indan-1-ylcarbamoyl}-oxetan-3-yl)-amide

Procedure

In analogy to the procedures described for the preparation of intermediate A-1 [B], 3-amino-oxetane-3-carboxylic acid{(S)-5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-indan-1-yl}-amide (example 49) was coupled with isoxazole-5-carboxylic acid to yield the title compound as yellow oil. MS: 538.1 (MH+, 1Cl).

Sources & evidence

ORD record
ord-fa7963438e2e47aa81ecf71f0e2c3a50
Source dataset
uspto-grants-2013_11
Patent number
US08592426B2

Reaction notes

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