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

HRID 2046577Notes

Reaction equation

HRID 2046577 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([F:30])[C:5]([C:24]2[N:28]=[C:27]([CH3:29])[O:26][N:25]=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([NH2:23])[CH2:22][CH2:21]2)=[O:19])[CH2:12][CH2:11]3)[CH:7]=1.[N:31]1[CH:36]=[C:35]([C:37](O)=[O:38])[CH:34]=[N:33][CH:32]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([F:30])[C:5]([C:24]2[N:28]=[C:27]([CH3:29])[O:26][N:25]=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:23][C:37]([C:35]4[CH:36]=[N:31][CH:32]=[N:33][CH:34]=4)=[O:38])[CH2:21][CH2:22]2)=[O:19])[CH2:12][CH2:11]3)[CH:7]=1

Participants

3

Reactant 2

HCID 78346Pyrimidine-5-carboxylic acidHCID 601425691-Amino-cyclopropanecarboxylic acid{(S)-5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-indan-1-yl}-amide

Product 1

HCID 60142570Pyrimidine-5-carboxylic acid (1-{(S)-5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-indan-1-ylcarbamoyl}-cyclopropyl)-amide

Procedure

In analogy to the procedures described for the preparation of intermediate A-1 [B], 1-amino-cyclopropanecarboxylic acid{(S)-5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-indan-1-yl}-amide (example 24) was coupled with pyrimidine-5-carboxylic acid to yield the title compound as yellow solid. MS: 533.2 (MH+, 1Cl).

Sources & evidence

ORD record
ord-e361c2d325234546957d26a4c24a7050
Source dataset
uspto-grants-2013_11
Patent number
US08592426B2

Reaction notes

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