3-Methoxy-1,2-oxazole-5-carboxylic acid → 3-Methoxy-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 2046602Notes

Reaction equation

HRID 2046602 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.[CH3:32][O:33][C:34]1[CH:38]=[C:37]([C:39](O)=[O:40])[O:36][N:35]=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:39]([C:37]4[O:36][N:35]=[C:34]([O:33][CH3:32])[CH:38]=4)=[O:40])[CH2:21][O:22][CH2:23]2)=[O:19])[CH2:12][CH2:11]3)[CH:7]=1

Participants

3

Reactant 2

HCID 3277173-Methoxy-1,2-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 601411823-Methoxy-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

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 3-methoxy-isoxazole-5-carboxylic acid to yield the title compound as light yellow viscous oil. MS: 568.1 (MH+, 1Cl).

Sources & evidence

ORD record
ord-ee279297a2fa4f23b35a6051227d47f4
Source dataset
uspto-grants-2013_11
Patent number
US08592426B2

Reaction notes

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