Dicyclohexylcarbodiimide → HCID 178496225, compound

HRID 255062Notes

Reaction equation

HRID 255062 reaction equation
Br.[CH3:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][N:9]1[C:13]([CH3:14])=[C:12]([CH3:15])[S:11][C:10]1=[NH:16].[C:17]12([C:27](O)=[O:28])[CH2:26][CH:21]3[CH2:22][CH:23]([CH2:25][CH:19]([CH2:20]3)[CH2:18]1)[CH2:24]2.C1(N=C=NC2CCCCC2)CCCCC1.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CC(N(C)C)=O>[CH3:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][N:9]1[C:13]([CH3:14])=[C:12]([CH3:15])[S:11]/[C:10]/1=[N:16]\[C:27]([C:17]12[CH2:26][CH:21]3[CH2:20][CH:19]([CH2:25][CH:23]([CH2:22]3)[CH2:24]1)[CH2:18]2)=[O:28]

Participants

7

Reactant 5

HCID 10868Dicyclohexylcarbodiimide2×HCID 132351-Adamantanecarboxylic acidHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 66858577HCID 66858577, compound

Product 1

HCID 178496225HCID 178496225, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °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 thiazolylidine 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, 6 H) 1.84 (d, J=2.50 Hz, 6 H) 1.94-2.02 (m, 3 H) 2.16 (s, 3 H) 2.22 (s, 3 H) 3.19 (s, 3 H) 3.39 (dd, J=5.62, 3.74 Hz, 2 H) 3.51 (dd, J=5.62, 3.74 Hz, 2 H) 3.73-3.77 (m, 2 H) 4.25 (t, J=5.46 Hz, 2 H); MS (ESI) m/z 393 (M=H)+.

Workup

  1. customwas used without purification
  2. filtrationThe mixture was filtered through Si-Carbonate (6 mL-1 g cartridge from Silicycle Chemical Division, MeOH wash)
  3. concentrationconcentrated to dryness
  4. customPurification by reverse phase HPLC

Sources & evidence

ORD record
ord-3f0d2f047e4c4ddeacfaba5a8342012e
Source dataset
uspto-grants-2011_01
Patent number
US07875639B2

Reaction notes

Loading…