1-Adamantanecarboxylic acid → HCID 178495143, compound

HRID 1469945Notes

Reaction equation

HRID 1469945 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][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>>[CH3:14][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: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]

Participants

4

Reactant 3

HCID 132351-Adamantanecarboxylic acidHCID 732382-Amino-4,5-dimethyl-1,3-thiazoleHCID 5245511-Bromo-3-methoxypropane

Product 1

HCID 178495143HCID 178495143, compoundYield 50%

Conditions

Temperature
85 °C

Procedure

A mixture of 4,5-dimethyl-thiazol-2-ylamine (0.20 g, 1.6 mmol) and 1-bromo-3-methoxypropane (0.28 g, 1.7 mmol) was heated at 85° C. for 14 hours. After cooling to ambient temperature, the unpurified residue (0.31 g, 1.1 mmol) and adamantane-1-carboxylic acid (0.22 g, 1.2 mmol) were processed as described in Example 3B. Purification by column chromatography (SiO2, 20-40% ethyl acetate/hexanes gradient) afforded 0.20 g (50%) of the title compound. 1H NMR (CDCl3, 300 MHz) δ ppm 1.69-1.79 (m, 6H), 1.90-2.00 (m, 6H), 2.00-2.10 (m, 5H), 2.18 (s, 3H), 2.19 (s, 3H), 3.33 (s, 3H), 3.40 (t, J=5.9 Hz, 2H), 4.22 (s, 2H); MS (DCI/NH3) m/z 363 (M+H)+. Anal. Calculated for C20H30N2O2S: C, 66.26; H, 8.34; N, 7.73. Found: C, 66.00; H, 8.60; N, 7.37.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customPurification by column chromatography (SiO2, 20-40% ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-c8ddb6c64e1d4e2891834df4ecffe3a3
Source dataset
uspto-grants-2015_04
Patent number
US09006275B2

Reaction notes

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