4-(1-adamantyl)-1,3-thiazol-2-amine → HCID 57756837, compound

HRID 228056Notes

Reaction equation

HRID 228056 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].[C:24]12([C:34]3[N:35]=[C:36]([NH2:39])[S:37][CH:38]=3)[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]3)[CH2:25]1)[CH2:31]2>>[C:24]12([C:34]3[N:35]=[C:36]([NH:39][C:1]([C:4]45[CH2:11][CH2:10][C:7]([NH:12][CH2:13][C:14]([N:16]6[CH2:20][C@@H:19]([F:21])[CH2:18][C@H:17]6[C:22]#[N:23])=[O:15])([CH2:8][CH2:9]4)[CH2:6][CH2:5]5)=[O:2])[S:37][CH:38]=3)[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]3)[CH2:25]1)[CH2:31]2

Participants

3

Reactant 2

HCID 6164344-(1-adamantyl)-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 57756837HCID 57756837, compoundYield 35.3%

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 4-adamantyl-2-aminothiazole (79.7 mg) were used to obtain (2S,4S)-1-[[N-[4-[N-(4-adamantylthiazol-2-yl)amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (29.5 mg).

Sources & evidence

ORD record
ord-de6230d21b5d4bcd9b858d7e05f808b5
Source dataset
uspto-grants-2009_07
Patent number
US07560569B2

Reaction notes

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