1-Adamantanecarboxylic acid → HCID 178435125, compound

HRID 1469943Notes

Reaction equation

HRID 1469943 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][O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:20]12([C:30](O)=[O:31])[CH2:29][CH:24]3[CH2:25][CH:26]([CH2:28][CH:22]([CH2:23]3)[CH2:21]1)[CH2:27]2>>[CH2:13]([O:12][CH2:11][CH2:10][N:3]1[C:2]([CH3:1])=[C:6]([CH3:7])[S:5]/[C:4]/1=[N:8]\[C:30]([C:20]12[CH2:29][CH:24]3[CH2:23][CH:22]([CH2:28][CH:26]([CH2:25]3)[CH2:27]1)[CH2:21]2)=[O:31])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 132351-Adamantanecarboxylic acidHCID 732382-Amino-4,5-dimethyl-1,3-thiazoleHCID 73833Benzene, ((2-bromoethoxy)methyl)-

Product 1

HCID 178435125HCID 178435125, compound

Procedure

4,5-Dimethylthiazol-2-ylamine, (2-Bromoethoxymethyl)-benzene and 1-adamantane carboxylic acid were processed as described in Example 47 to afford the title compound. 1H NMR (CDCl3, 300 MHz) δ ppm 1.58-1.73 (m, 6H) 1.79 (d, J=2.50 Hz, 6H) 1.91-2.02 (m, 3H) 2.15 (s, 3H) 2.22 (s, 3H) 3.77 (t, J=5.46 Hz, 2H) 4.29 (t, J=5.46 Hz, 2H) 4.47 (s, 2H) 7.19 (d, J=6.55 Hz, 2H) 7.22-7.33 (m, 3H); MS (ESI) m/z 425 (M=H)+.

Sources & evidence

ORD record
ord-1f094837dc014dfca7bbc08e9a25fabe
Source dataset
uspto-grants-2015_04
Patent number
US09006275B2

Reaction notes

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