Cyclopropanecarbonyl chloride → HCID 178517406, compound

HRID 1958028Notes

Reaction equation

HRID 1958028 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[S:5][C:6]=1[C:7]([NH2:9])=[O:8].[CH:16]1([C:19](Cl)=O)[CH2:18][CH2:17]1>ClCCl>[CH:16]1([C:19]2[NH:1][C:2]3[N:3]=[C:4]([N:10]4[CH2:15][CH2:14][O:13][CH2:12][CH2:11]4)[S:5][C:6]=3[C:7](=[O:8])[N:9]=2)[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 13595332HCID 13595332, compound

Product 1

HCID 178517406HCID 178517406, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-amino-2-(4-morpholinyl)-1,3-thiazole-5-carboxamide (0.15 g, 0.657 mmol) in Dichloromethane (DCM) (2 ml) at 0° C. was added cyclopropanecarbonyl chloride (0.075 ml, 0.821 mmol) dropwise. The mixture was stirred at room temperature overnight, and then concentrated. To the resulting residue was added ethanol (1 mL) and 6N NaOH (0.8 mL). The mixture was stirred at room temperature for 3 h, and then acidified with 6N HCl (0.7 mL) to pH ˜5. The precipitate was collected, rinsed with water, and dried in vacuo to furnish crude 5-cyclopropyl-2-(4-morpholinyl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one. (90 mg, 49%); LC/MS: MS (ES) m/e 279 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 0.99-1.06 (m, 4H), 1.95 (ddd, J=10.6, 2.0, 1.8 Hz, 1H) 3.53-3.59 (m, 4H) 3.68-3.76 (m, 4H) 12.56 (br, s, 1H).

Workup

  1. concentrationconcentrated
  2. additionTo the resulting residue was added ethanol (1 mL) and 6N NaOH (0.8 mL)
  3. stirringThe mixture was stirred at room temperature for 3 h
  4. customThe precipitate was collected
  5. washrinsed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-0500cdf2b0cb434fb5ccd197453eb9a3
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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