1-Adamantanecarboxylic acid → HCID 178435120, compound

HRID 255104Notes

Reaction equation

HRID 255104 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH2:8])[S:5][C:6]=1[CH3:7].Br[CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.[C:18]12([C:28](O)=[O:29])[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:26][CH:20]([CH2:21]3)[CH2:19]1)[CH2:25]2>>[CH:12]1([CH2:11][CH2:10][N:3]2[C:2]([CH3:1])=[C:6]([CH3:7])[S:5]/[C:4]/2=[N:8]\[C:28]([C:18]23[CH2:27][CH:22]4[CH2:21][CH:20]([CH2:26][CH:24]([CH2:23]4)[CH2:25]2)[CH2:19]3)=[O:29])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 3

HCID 132351-Adamantanecarboxylic acidHCID 15440(2-Bromoethyl)cyclohexaneHCID 732382-Amino-4,5-dimethyl-1,3-thiazole

Product 1

HCID 178435120HCID 178435120, compound

Procedure

4,5-Dimethylthiazol-2-ylamine, (2-bromoethyl)-cyclohexane and 1-adamantane carboxylic acid were processed according to the method of Example 47 to afford the title compound. 1H NMR (CDCl3, 500 MHz) δ ppm 0.93-1.05 (m, 2 H) 1.10-1.26 (m, 3 H) 1.29-1.38 (m, 1 H) 1.48-1.57 (m, 2 H) 1.58-1.75 (m, 9 H) 1.75-1.83 (m, J=12.79 Hz, 2 H) 1.85 (d, J=2.50 Hz, 6 H) 1.94-2.02 (m, 3 H) 2.15 (s, 3 H) 2.20 (s, 3 H) 4.07-4.18 (m, 2 H); MS (ESI) m/z 401 (M+H)+.

Sources & evidence

ORD record
ord-53877c0c8db04268bec625b6d03559dd
Source dataset
uspto-grants-2011_01
Patent number
US07875639B2

Reaction notes

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