1-Adamantanecarboxylic acid → HCID 178498882, compound

HRID 1469933Notes

Reaction equation

HRID 1469933 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]([NH2:10])=[N:7][CH:6]=1)=[O:4].[C:11]12([C:21](O)=[O:22])[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH2:12]1)[CH2:18]2>>[CH3:1][O:2][C:3]([C:5]1[S:9][C:8](=[N:10][C:21]([C:11]23[CH2:20][CH:15]4[CH2:14][CH:13]([CH2:19][CH:17]([CH2:16]4)[CH2:18]2)[CH2:12]3)=[O:22])[NH:7][CH:6]=1)=[O:4]

Participants

3

Reactant 2

HCID 132351-Adamantanecarboxylic acidHCID 238005Methyl 2-aminothiazole-5-carboxylate

Product 1

HCID 178498882HCID 178498882, compoundYield 357.5%

Procedure

2-Amino-thiazole-5-carboxylic acid methyl ester (1.58 g, 10.0 mmole) and 1-adamantanecarboxylic acid (1.98 g, 1.1 mmol) were processed as described in Example 3B to afford 1.26 g (49%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.62-1.79 (m, 6H) 1.86 (d, J=3 Hz, 6H) 1.99 (s, 3H) 3.26 (s, 3H) 3.64-3.81 (s, 3H) 8.30 (s, 1H); MS (DCI/NH3) m/z 321 (M+H).

Sources & evidence

ORD record
ord-3ed715e38f2845ff983ae6f084572070
Source dataset
uspto-grants-2015_04
Patent number
US09006275B2

Reaction notes

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