Triphenylphosphine → HCID 67437763, compound

HRID 2089448Notes

Reaction equation

HRID 2089448 reaction equation
[N:1]([CH:4]1[CH2:9][CH2:8][CH:7]([C:10]2[N:14]([CH3:15])[N:13]=[CH:12][C:11]=2[NH:16][C:17]([C:19]2[N:20]=[C:21]([C:32]3[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:33]=3[F:39])[S:22][C:23]=2[NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:18])[CH2:6][CH2:5]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[NH2:1][CH:4]1[CH2:5][CH2:6][CH:7]([C:10]2[N:14]([CH3:15])[N:13]=[CH:12][C:11]=2[NH:16][C:17]([C:19]2[N:20]=[C:21]([C:32]3[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:33]=3[F:39])[S:22][C:23]=2[NH:24][C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:30])[CH3:28])=[O:18])[CH2:8][CH2:9]1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 86658428HCID 86658428, compound

Product 1

HCID 67437763HCID 67437763, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

tert-Butyl 4-(5-(4-azidocyclohexyl)-1-methyl-1H-pyrazol-4-ylcarbamoyl)-2-(2,6-difluorophenyl)thiazol-5-ylcarbamate (18 mg, 0.032 mmol) was dissolved in THF (2 mL) and water (0.5 mL). Triphenylphosphine (21.5 mg, 0.083 mmol) was added and the mixture was heated at 60° C. overnight. After cooling to room temperature, the reaction was quenched with water and extracted with methylene chloride three times to give the crude product tert-butyl 4-(5-(4-aminocyclohexyl)-1-methyl-1H-pyrazol-4-ylcarbamoyl)-2-(2,6-difluorophenyl)thiazol-5-ylcarbamate.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction was quenched with water
  3. extractionextracted with methylene chloride three times

Sources & evidence

ORD record
ord-6023adbac4074f28b9f120407335dcd7
Source dataset
uspto-grants-2013_05
Patent number
US08436001B2

Reaction notes

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