1-Adamantanecarboxylic acid → HCID 178435121, compound

HRID 1469991Notes

Reaction equation

HRID 1469991 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][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1.[C:21]12([C:31](O)=[O:32])[CH2:30][CH:25]3[CH2:26][CH:27]([CH2:29][CH:23]([CH2:24]3)[CH2:22]1)[CH2:28]2>>[NH:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12]([CH2:11][CH2:10][N:3]2[C:2]([CH3:1])=[C:6]([CH3:7])[S:5]/[C:4]/2=[N:8]\[C:31]([C:21]23[CH2:30][CH:25]4[CH2:24][CH:23]([CH2:29][CH:27]([CH2:26]4)[CH2:28]2)[CH2:22]3)=[O:32])=[CH:13]1

Participants

4

Reactant 3

HCID 132351-Adamantanecarboxylic acidHCID 732382-Amino-4,5-dimethyl-1,3-thiazoleHCID 769243-(2-Bromoethyl)indole

Product 1

HCID 178435121HCID 178435121, compound

Procedure

4,5-Dimethylthiazol-2-ylamine, 3-(2-bromo-ethyl)-1H-indole 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 1.68-1.75 (m, 6H) 1.91 (d, J=2.50 Hz, 6H) 1.98-2.04 (m, 3H) 2.13 (d, J=4.68 Hz, 6H) 3.04-3.21 (m, 2H) 4.20-4.43 (m, 2H) 6.98 (t, J=7.49 Hz, 1H) 7.09 (t, J=7.64 Hz, 1H) 7.17 (d, J=2.18 Hz, 1H) 7.36 (d, J=8.11 Hz, 1H) 7.68 (d, J=7.80 Hz, 1H) 10.88 (s, 1H); MS (ESI) m/z 434 (M+H)+.

Sources & evidence

ORD record
ord-6aef0878d0624e609d53ab5050e3ed0d
Source dataset
uspto-grants-2015_04
Patent number
US09006275B2

Reaction notes

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