Triethylamine → HCID 59474060, compound

HRID 1660762Notes

Reaction equation

HRID 1660762 reaction equation
[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9][NH2:10])([CH3:4])([CH3:3])[CH3:2].Br[C:13]1[S:14][C:15]([C:22]2[C:23]([CH3:37])=[N:24][N:25]3[C:30]([CH:31]([CH2:34][CH3:35])[CH2:32][CH3:33])=[CH:29][C:28]([CH3:36])=[N:27][C:26]=23)=[C:16]([C:18]([F:21])([F:20])[F:19])[N:17]=1.C(N(CC)CC)C>CO>[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9][NH:10][C:13]1[S:14][C:15]([C:22]2[C:23]([CH3:37])=[N:24][N:25]3[C:30]([CH:31]([CH2:32][CH3:33])[CH2:34][CH3:35])=[CH:29][C:28]([CH3:36])=[N:27][C:26]=23)=[C:16]([C:18]([F:19])([F:21])[F:20])[N:17]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 187201N-BOC-ethylenediamineHCID 67429934HCID 67429934, compound

Product 1

HCID 59474060HCID 59474060, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

Add (2-amino-ethyl)-carbamic acid tert-butyl ester (0.5 mL, 506 mg, 3.2 mmol) to a solution of 3-(2-bromo-4-trifluoromethyl-thiazol-5-yl)-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine (100 mg, 0.22 mmol) and triethylamine (0.3 mL, 222 mg, 2.2 mmol) in methanol (1 mL). Evaporate off the methanol and heat to 80° C. overnight. Cool the reaction to room temperature and concentrate under vacuum. Purify the resulting residue by column chromatography, eluting with 10-50% ethyl acetate in CH2Cl2, to give the title compound (0.11 g, 97%). ES/MS m/z 527.2 (M+1)+.

Workup

  1. customEvaporate off the methanol
  2. temperatureCool
  3. customthe reaction to room temperature
  4. concentrationconcentrate under vacuum
  5. customPurify the resulting residue by column chromatography
  6. washeluting with 10-50% ethyl acetate in CH2Cl2

Sources & evidence

ORD record
ord-2f063736bddf4fbca7a8065b1626464d
Source dataset
uspto-grants-2011_10
Patent number
US08030304B2

Reaction notes

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