4-Cyclopropyl-1,3-thiazol-2-amine → (2S,4S)-1-[[N-[4-[N-(4-cyclopropylthiazol-2-yl)amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

HRID 227997Notes

Reaction equation

HRID 227997 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)([OH:3])=O.[NH2:24][C:25]1[S:26][CH:27]=[C:28]([CH:30]2[CH2:32][CH2:31]2)[N:29]=1>>[CH:30]1([C:28]2[N:29]=[C:25]([NH:24][C:1]([C:4]34[CH2:11][CH2:10][C:7]([NH:12][CH2:13][C:14]([N:16]5[CH2:20][C@@H:19]([F:21])[CH2:18][C@H:17]5[C:22]#[N:23])=[O:15])([CH2:6][CH2:5]3)[CH2:8][CH2:9]4)=[O:3])[S:26][CH:27]=2)[CH2:32][CH2:31]1

Participants

3

Reactant 2

HCID 6744564-Cyclopropyl-1,3-thiazol-2-amineHCID 57634365(2S,4S)-1-[[N-(4-carboxybicyclo[2,2,2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

Product 1

HCID 57756758(2S,4S)-1-[[N-[4-[N-(4-cyclopropylthiazol-2-yl)amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrileYield 62.6%

Procedure

In a similar manner to Example 87, (2S,4S)-1-[[N-(4-carboxybicyclo[2.2.2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (50.0 mg) and 2-amino-4-cyclopropylthiazole (47.7 mg) were used to obtain (2S,4S)-1-[[N-[4-[N-(4-cyclopropylthiazol-2-yl)amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (43.1 mg).

Sources & evidence

ORD record
ord-0f6e15cbb0094537b439a64f17cc2b8a
Source dataset
uspto-grants-2009_07
Patent number
US07560569B2

Reaction notes

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