2-Amino-4,5-dimethyl-1,3-thiazole → HCID 66858577, compound
Reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH2:8])[S:5][C:6]=1[CH3:7].[Br:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH3:16]>>[BrH:9].[CH3:16][O:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][N:3]1[C:2]([CH3:1])=[C:6]([CH3:7])[S:5][C:4]1=[NH:8]Participants
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 4,5-Dimethylthiazol-2-ylamine (20 mg, 0.16 mmol) and 1-bromo-2-(2-methoxyethoxy)ethane (0.20 mmol) was heated at 80° C. overnight to afford 3-[2-(2-methoxyethoxy)-ethyl]-4,5-dimethyl-1,3-thiazol-2(3H)-ylideneamine hydrobromide, which was used without purification. The alkylated thiazolylidene hydrobromide (1.25 equiv), 1-adamantane carboxylic acid (1.0 equiv), polymer-bound dicyclohexylcarbodiimide (PS-DCC, 3 equiv), 1-hydroxybenzotriazole hydrate (HOBT, 1 equiv), N,N-diisopropylethylamine (3 equiv), were combined in dimethylacetamide (DMA, 2.8 mL) and heated in a microwave to 100° C. for 420 seconds. The mixture was filtered through Si-Carbonate (6 mL-1 g cartridge from Silicycle Chemical Division, MeOH wash) and then concentrated to dryness. Purification by reverse phase HPLC afforded the title compound. 1H NMR (DMSO-d6, 500 MHz) δ ppm 11.68 (q, J=12.27 Hz, 6H) 1.84 (d, J=2.50 Hz, 6H) 1.94-2.02 (m, 3H) 2.16 (s, 3H) 2.22 (s, 3H) 3.19 (s, 3H) 3.39 (dd, J=5.62, 3.74 Hz, 2H) 3.51 (dd, J=5.62, 3.74 Hz, 2H) 3.73-3.77 (m, 2H) 4.25 (t, J=5.46 Hz, 2H); MS (ESI) m/z 393 (M=H)+.
Sources & evidence
- ORD record
- ord-f56c6f87eb214439aaf2e85faf18ab47
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09006275B2
Reaction notes
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