Hydrochloric Acid → HCID 131729207, compound

HRID 1660749Notes

Reaction equation

HRID 1660749 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[S:5][C:6]=1[C:7]1[C:8]([CH3:22])=[N:9][N:10]2[C:15]([CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:14][C:13]([CH3:21])=[N:12][C:11]=12.Cl>CC(C)=O.Cl>[ClH:1].[Cl:1][C:2]1[N:3]=[C:4]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[S:5][C:6]=1[C:7]1[C:8]([CH3:22])=[N:9][N:10]2[C:15]([CH:16]([CH2:17][CH3:18])[CH2:19][CH3:20])=[CH:14][C:13]([CH3:21])=[N:12][C:11]=12

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 248989774-(4-Chloro-5-(2,5-dimethyl-7-(pentan-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)thiazol-2-yl)morpholine

Product 1

HCID 131729207HCID 131729207, compoundYield 151.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 180AcetoneSolvent

Procedure

Dissolve 3-(4-chloro-2-morpholin-4-yl-thiazol-5-yl)-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine (1.40 g, 3.33 mmol) in acetone (10 mL) at 50° C. and cool to room temperature. Add hydrogen chloride (2 M in diethyl ether, 2.0 mL, 4.0 mmol) and stir well in a sonicator. Concentrate the solution a little and add a minimal amount of diethyl ether to crystallize the HCl salt. Cool the mixture in a refrigerator overnight. Add additional hydrogen chloride (2 M in diethyl ether, 2.0 mL, 4 0 mmol) and cool in a refrigerator. Filter the crystalline material and dry to obtain the title compound (1.15 g, 75%). ES/MS m/z (35Cl) 420 (M+1)+; 1H NMR(CDCl3): 9.18 (br, 1H), 6.86 (s, 1H), 3.72 (m, 4H), 3.49(m, 1H), 3.39 (m, 4H), 2.48 (s, 3H), 2.38(s, 3H), 1.79 (m, 4H), 0.79 (m, 6H).

Workup

  1. concentrationConcentrate the solution a little and
  2. additionadd a minimal amount of diethyl ether
  3. customto crystallize the HCl salt
  4. temperatureCool the mixture in a refrigerator overnight
  5. temperaturecool in a refrigerator
  6. filtrationFilter the crystalline material
  7. customdry

Sources & evidence

ORD record
ord-bc0a32e0d48d4012bdd12cc0636ff7f2
Source dataset
uspto-grants-2011_10
Patent number
US08030304B2

Reaction notes

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