Potassium Carbonate → HCID 16059372, compound

HRID 1710629Notes

Reaction equation

HRID 1710629 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([Cl:19])=[CH:13][CH:12]=2)[CH2:7][C@@H:6]1[CH3:20])=[O:4].[Cl:21][C:22]1[CH:31]=[CH:30][C:25]2[NH:26][C:27](=[O:29])[O:28][C:24]=2[CH:23]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:21][C:22]1[CH:31]=[CH:30][C:25]2[N:26]([CH2:2][C:3]([N:5]3[CH2:10][CH2:9][N:8]([C:11]4[CH:12]=[CH:13][C:14]([Cl:19])=[C:15]([O:17][CH3:18])[CH:16]=4)[CH2:7][C@@H:6]3[CH3:20])=[O:4])[C:27](=[O:29])[O:28][C:24]=2[CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 298586-Chloro-2,3-dihydrobenzoxazol-2-oneHCID 57840175HCID 57840175, compound

Product 1

HCID 16059372HCID 16059372, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 9 was prepared according to the procedure described in Example 2 using 2-chloro-1-[(S)-4-(4-chloro-5-methoxy-phenyl)-2-methyl-piperazin-1-yl]-ethanone (8), 6-chloro-3H-benzooxazol-2-one and K2CO3 in DMF: HPLC retention time, 2.75 minutes (Agilent Zorbax SB-C18, 2.1×50 mm, 5μ, 35° C.) using 1 ml/min flow rate, a 2.5 minute gradient of 20% to 100% B with a 1.1 minute wash at 100% B (A=0.1% formic acid/5% acetonitrile/94.9% water, B=0.1% formic acid/5% water/94.9% acetonitrile); MS (ES) M+H expected, 450.4, found, 450.4.

Workup

  1. customHPLC retention time, 2.75 minutes (Agilent Zorbax SB-C18, 2.1×50 mm, 5μ, 35° C.)
  2. washa 2.5 minute gradient of 20% to 100% B with a 1.1 minute wash at 100% B (A=0.1% formic acid/5% acetonitrile/94.9% water, B=0.1% formic acid/5% water/94.9% acetonitrile)

Sources & evidence

ORD record
ord-9c8c71871f9841228562ee6adc7c32e2
Source dataset
uspto-grants-2010_09
Patent number
US07790726B2

Reaction notes

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