Pyridine → HCID 90020062, compound

HRID 2200097Notes

Reaction equation

HRID 2200097 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[N:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]([CH:16]3[CH2:18][CH2:17]3)=[O:15])[CH:8]=2)=[CH:4][C:3]=1[CH3:21].N1C=CC=CC=1.C1COCC1.Cl[C:34]([O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:35]>O.CCOC(C)=O.C(Cl)Cl>[CH:16]1([C:14]([NH:13][C:9]2[N:10]=[CH:11][N:12]=[C:7]([O:6][C:5]3[CH:19]=[CH:20][C:2]([NH:1][C:34](=[O:35])[O:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[C:3]([CH3:21])[CH:4]=3)[CH:8]=2)=[O:15])[CH2:17][CH2:18]1

Participants

8

Reactant 4

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 15891Phenyl chloroformateHCID 90020675HCID 90020675, compound2×

Product 1

HCID 90020062HCID 90020062, compoundYield 98.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Add N-[6-(4-amino-3-methyl-phenoxy)pyrimidin-4-yl]cyclopropanecarboxamide (Intermediate A1, 500 mg, 1.76 mmol), pyridine (280 mg, 3.52 mmol) to a mixed solvent of THF (5 mL) and DCM (5 mL). Cool to 0° C.; add slowly phenyl chloroformate (330 mg, 2.11 mmol). Stir the reaction at room temperature for 2 hrs. TLC (EtOAc:PE=1:1) shows the reaction is complete. Dilute with water, extract with DCM. Combine the organic layers, wash with 1M diluted HCl, brine sequentially, and dry over anhydrous Na2SO4. Concentration under reduced pressure affords the title compound (700 mg, 98.3%). MS: (M+1) 273.

Workup

  1. customthe reaction at room temperature for 2 hrs
  2. extractionextract with DCM
  3. washwash with 1M diluted HCl, brine sequentially
  4. dry with materialdry over anhydrous Na2SO4
  5. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-2146fbdf5d2e4531872302758448c62c
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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