Trifluoroacetic acid → (3-(Methylsulfinyl)-1-(5-phenylpyrimidin-2-yl)-1H-indol-6-yl)(piperazin-1-yl)methanone

HRID 630449Notes

Reaction equation

HRID 630449 reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][S:9]([C:11]1[C:19]2[C:14](=[CH:15][C:16]([C:20]([N:22]3[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]3)=[O:21])=[CH:17][CH:18]=2)[N:13]([C:35]2[N:40]=[CH:39][C:38]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[CH:37][N:36]=2)[CH:12]=1)=[O:10].C(=O)([O-])O.[Na+]>ClCCl.O>[CH3:8][S:9]([C:11]1[C:19]2[C:14](=[CH:15][C:16]([C:20]([N:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[O:21])=[CH:17][CH:18]=2)[N:13]([C:35]2[N:36]=[CH:37][C:38]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[CH:39][N:40]=2)[CH:12]=1)=[O:10]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 131735391tert-Butyl 4-(3-(methylsulfinyl)-1-(5-phenylpyrimidin-2-yl)-1H-indole-6-carbonyl)piperazine-1-carboxylate

Product 1

HCID 118666184(3-(Methylsulfinyl)-1-(5-phenylpyrimidin-2-yl)-1H-indol-6-yl)(piperazin-1-yl)methanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

TFA (0.5 mL) was added to compound 12d) (170 mg, 0.311 mmol) in dichloromethane (5 mL) at room temperature and the solution was stirred for 2 h. The reaction mixture was then diluted with water, adjusted to pH 8 via addition of saturated sodium hydrogen carbonate solution and extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and evaporated. The remnant was purified by preparative TLC using a blend of 5% methanol in dichloromethane as eluent. White solid. Yield: 75 mg (51% of theory). Melting range: 193-197° C. HPLC (method 3): Rt=4.02 min. Mass spectroscopy: m/z: [M+H]+=446.1.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. customevaporated
  4. customThe remnant was purified by preparative TLC

Sources & evidence

ORD record
ord-a176c6982bb447b5b8fb635e2be6b840
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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