1-Adamantanecarboxylic acid → HCID 178467909, compound

HRID 1469942Notes

Reaction equation

HRID 1469942 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][CH3:14].[C:15]12([C:25](O)=[O:26])[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]3)[CH2:16]1)[CH2:22]2>>[CH2:11]([O:12][CH2:13][CH2:14][N:3]1[C:2]([CH3:1])=[C:6]([CH3:7])[S:5]/[C:4]/1=[N:8]\[C:25]([C:15]12[CH2:24][CH:19]3[CH2:18][CH:17]([CH2:23][CH:21]([CH2:20]3)[CH2:22]1)[CH2:16]2)=[O:26])[CH3:10]

Participants

4

Reactant 3

HCID 132351-Adamantanecarboxylic acidHCID 611412-Bromoethyl ethyl etherHCID 732382-Amino-4,5-dimethyl-1,3-thiazole

Product 1

HCID 178467909HCID 178467909, compound

Procedure

4,5-Dimethylthiazol-2-ylamine, 1-bromo-2-ethoxyethane and 1-adamantane carboxylic acid were processed as described in Example 47 to afford the title compound. 1H NMR (CDCl3, 500 MHz) δ ppm 1.05 (t, J=7.02 Hz, 3H) 1.61-1.76 (m, 6H) 1.84 (d, J=2.50 Hz, 6H) 1.95-2.03 (m, 3H) 2.16 (s, 3H) 2.21 (s, 3H) 3.43 (q, J=7.07 Hz, 2H) 3.69 (t, J=5.46 Hz, 2H) 4.24 (t, J=5.46 Hz, 2H); MS (ESI) m/z 363 (M=H)+.

Sources & evidence

ORD record
ord-6b0ed7879f844dceb6c62c096094c228
Source dataset
uspto-grants-2015_04
Patent number
US09006275B2

Reaction notes

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