4-Thiazoleacetic acid, 2-amino-, ethyl ester → HCID 87598220, compound

HRID 227987Notes

Reaction equation

HRID 227987 reaction equation
[C:1]([C:4]12[CH2:11][CH2:10][C:7]([NH:12][CH2:13][C:14]([N:16]3[CH2:20][C@@H:19]([F:21])[CH2:18][C@H:17]3[C:22]#[N:23])=[O:15])([CH2:8][CH2:9]1)[CH2:6][CH2:5]2)(O)=[O:2].[NH2:24][C:25]1[S:26][CH:27]=[C:28]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[N:29]=1>>[CH2:34]([O:33][C:31]([CH2:30][C:28]1[N:29]=[C:25]([NH:24][C:1]([C:4]23[CH2:9][CH2:8][C:7]([NH:12][CH2:13][C:14]([N:16]4[CH2:20][C@@H:19]([F:21])[CH2:18][C@H:17]4[C:22]#[N:23])=[O:15])([CH2:6][CH2:5]2)[CH2:10][CH2:11]3)=[O:2])[S:26][CH:27]=1)=[O:32])[CH3:35]

Participants

3

Reactant 2

HCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl esterHCID 57634365(2S,4S)-1-[[N-(4-carboxybicyclo[2,2,2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

Product 1

HCID 87598220HCID 87598220, compoundYield 14.7%

Procedure

In a similar manner to Example 63, (2S,4S)-1-[[N-(4-carboxybicyclo[2.2.2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (50.0 mg) and ethy 2-aminothiazole-4-acetate (63.3 mg) were used to obtain (2S,4S)-1-[[N-[4-[N-(4-ethoxycarbonylmethylthiazol-2-yl)amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (11.2 mg).

Sources & evidence

ORD record
ord-f750c00ee7564600b9d255d9228d9093
Source dataset
uspto-grants-2009_07
Patent number
US07560569B2

Reaction notes

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