1-Adamantanecarboxylic acid → HCID 178435123, compound

HRID 1469948Notes

Reaction equation

HRID 1469948 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][CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=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>>[CH2:14]([O:13][CH2:12][CH2:11][CH2:10][N:3]1[C:2]([CH3:1])=[C:6]([CH3:7])[S:5]/[C:4]/1=[N:8]\[C:31]([C:21]12[CH2:30][CH:25]3[CH2:24][CH:23]([CH2:29][CH:27]([CH2:26]3)[CH2:28]1)[CH2:22]2)=[O:32])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 132351-Adamantanecarboxylic acidHCID 732382-Amino-4,5-dimethyl-1,3-thiazoleHCID 2776064Benzyl 3-Bromopropyl Ether

Product 1

HCID 178435123HCID 178435123, compound

Procedure

4,5-Dimethylthiazol-2-ylamine, (3-bromo-propoxymethyl)-benzene and 1-adamantane carboxylic acid were processed as described in Example 47 to afford the title compound. 1H NMR (CDCl3, 500 MHz) δ ppm 1.57-1.73 (m, 6H) 1.79-1.85 (m, 6H) 1.91-1.96 (m, 3H) 1.96-2.04 (m, 2H) 2.12-2.17 (m, 3H) 2.18-2.22 (m, 3H) 3.51 (t, J=5.93 Hz, 2H) 4.20 (t, 2H) 4.46 (s, 2H) 7.25-7.38 (m, 5H); MS (ESI) m/z 439 (M+H)+.

Sources & evidence

ORD record
ord-54864a30c3874ad29f62cfa6af9b07c9
Source dataset
uspto-grants-2015_04
Patent number
US09006275B2

Reaction notes

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