Diisopropylethylamine → HCID 46940287, compound

HRID 1095912Notes

Reaction equation

HRID 1095912 reaction equation
Cl[C:2]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)=[O:3].C(N(CC)C(C)C)(C)C.[NH2:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]([CH3:44])[C:31]([C:37]2[CH:42]=[CH:41][N:40]=[C:39]([Cl:43])[CH:38]=2)([OH:36])[C:32]([F:35])([F:34])[F:33])=[C:26]([Cl:45])[CH:25]=1.ClC(C1C=CC(C([O-])=O)=CC=1)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:11][O:10][C:8](=[O:9])[C:7]1[CH:12]=[CH:13][C:4]([C:2]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([CH:30]([CH3:44])[C:31]([C:37]3[CH:42]=[CH:41][N:40]=[C:39]([Cl:43])[CH:38]=3)([OH:36])[C:32]([F:33])([F:34])[F:35])=[C:26]([Cl:45])[CH:25]=2)=[O:3])=[CH:5][CH:6]=1

Participants

7

Reactant 5

HCID 81531Diisopropylethylamine2×HCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 516892Sodium BicarbonateHCID 17979044HCID 17979044, compoundHCID 866291093-(4-Amino-2-chloro-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol

Product 1

HCID 46940287HCID 46940287, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methyl 4-chlorocarbonylbenzoate (CAS Reg. No. 7377-26-6, 30 mg) and N,N-diisopropylethylamine (0.05 ml) in DCM (5 ml) was added to a solution of 3-(4-amino-2-chloro-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol (50 mg) in DCM (1 ml). The mixture was stirred for 2 h at room temperature. Additional 4-chlorocarbonylbenzoate (CAS Reg. No. 7377-26-6, 54 mg) and N,N-diisopropylethylamine (0.1 ml) were added. The mixture was stirred for 4 h at room temperature. The mixture was poured on a saturated aqueous NaHCO3 solution (20 ml) and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and then concentrated to an oil. The residue was purified by flash chromatography (SiO2, 0 to 30% EtOAc/heptane) to give the title compound (57 mg) as a white foam. MS (m/e)=527.0 [M+H+].

Workup

  1. stirringThe mixture was stirred for 4 h at room temperature
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated to an oil
  5. customThe residue was purified by flash chromatography (SiO2, 0 to 30% EtOAc/heptane)

Sources & evidence

ORD record
ord-d69974b86a15468eb2a358a4a3a399d8
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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