Trifluoroacetic acid → HCID 68486103, compound

HRID 1891217Notes

Reaction equation

HRID 1891217 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O.CCN([CH:36]([CH3:38])[CH3:37])C(C)C.C1(C(Cl)=O)CC1>C(Cl)Cl>[CH:36]1([C:6]([N:8]2[CH2:13][CH:12]=[C:11]([C:14]3[CH:15]=[CH:16][C:17]([CH:20]([OH:22])[CH3:21])=[CH:18][CH:19]=3)[CH2:10][CH2:9]2)=[O:7])[CH2:38][CH2:37]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acid2×HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 11243547HCID 11243547, compound

Product 1

HCID 68486103HCID 68486103, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the title compound from Example 9 Step A (301 mg, 1.00 mmol) in DCM (6 mL) was added TFA (3 mL). After 15 min, the reaction mixture was concentrated in vacuo, and the crude TFA salt was used without further purification. To a solution of the crude TFA salt in DCM (5 mL) were added DIEA (263 μL, 15.1 mmol) and cyclopropanecarbonyl chloride (274 μL, 3.01 mmol), and the resulting mixture was allowed to stir at room temperature. After 45 min, the reaction mixture was quenched by addition of sat aq NaHCO3 and the aqueous phase was extracted with DCM. The organic phase was separated and concentrated in vacuo to provide the crude amide, which was used without further purification: LCMS m/z 270.5 [M+H]+. To a solution of the crude amide in MeOH (10 mL) was added NaBH4 (171 mg, 4.52 mmol), and the mixture was stirred at room temperature. After 20 min, the reaction mixture was concentrated in vacuo and was redissolved in EtOAc. The mixture was washed with sat aq NH4Cl, and the organic phase was separated, dried over sodium sulfate, and concentrated in vacuo. The crude alcohol was used without further purification: LCMS m/z 272.5 [M+H]+.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customthe crude TFA salt was used without further purification
  3. waitAfter 45 min
  4. customthe reaction mixture was quenched by addition of sat aq NaHCO3
  5. extractionthe aqueous phase was extracted with DCM
  6. customThe organic phase was separated
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-81d5f1b22d544ccfbef3f93ac6e57464
Source dataset
uspto-grants-2013_08
Patent number
US08507512B2

Reaction notes

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