Water → HCID 71270885, compound

HRID 510394Notes

Reaction equation

HRID 510394 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH2:8])[N:5]2[N:9]=[CH:10][C:11]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=3[Cl:20])=[C:4]2[N:3]=1.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.O>C(O)C>[Cl:20][C:14]1[C:15]([Cl:19])=[CH:16][CH:17]=[CH:18][C:13]=1[CH2:12][C:11]1[CH:10]=[N:9][N:5]2[C:6]([NH2:8])=[CH:7][C:2]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[N:3][C:4]=12

Participants

5

Reactant 3

HCID 962WaterHCID 8083MorpholineHCID 86724879HCID 86724879, compound

Product 1

HCID 71270885HCID 71270885, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

5-chloro-3-[(2,3-dichlorophenyl)methyl]pyrazolo[1,5-a]pyrimidin-7-amine (1.7 g, 4.43 mmol) and morpholine (1.36 g, 15.6 mmol) were mixed in ethanol (10 mL) in a microwave tube. The reaction mixture was irradiated (microwave) and stirred at 150° C. for 3 hours. Reaction mixture was dropped into cold water (100 mL) to precipitate while stirring. Precipitate was collected by filtration. It was washed with water (10 mL) and dried. The titled product was obtained. (1.90 g, 97%); LC/MS: MS (ES+) m/e 378 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 3.43 (br. s., 1H) 3.45 (d, J=5.05 Hz, 3H) 3.63-3.71 (m, 4H) 4.00 (s, 2H) 5.55 (s, 1H) 7.16 (s, 2H) 7.22-7.30 (m, 1H) 7.30-7.40 (m, 1H) 7.46 (dd, J=7.83, 1.77 Hz, 1H) 7.72 (s, 1H).

Workup

  1. customThe reaction mixture was irradiated (microwave)
  2. customReaction mixture
  3. customto precipitate
  4. stirringwhile stirring
  5. filtrationPrecipitate was collected by filtration
  6. washIt was washed with water (10 mL)
  7. customdried

Sources & evidence

ORD record
ord-c7e9e7ded32140faaf6aac512ad0ddfd
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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