Water → HCID 59278376, compound

HRID 559655Notes

Reaction equation

HRID 559655 reaction equation
[N:1]([CH2:4][CH2:5][C@H:6]([NH:17][C:18]([C:20]1[C:21]2[CH:28]=[N:27][N:26]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[C:22]=2[CH:23]=[N:24][CH:25]=1)=[O:19])[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:8]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.C(#N)C>C1COCC1>[NH2:1][CH2:4][CH2:5][C@H:6]([NH:17][C:18]([C:20]1[C:21]2[CH:28]=[N:27][N:26]([C:29]3[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=3)[C:22]=2[CH:23]=[N:24][CH:25]=1)=[O:19])[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([S:13]([CH3:16])(=[O:14])=[O:15])[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 11776TriphenylphosphineHCID 86640802HCID 86640802, compound

Product 1

HCID 59278376HCID 59278376, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a room temperature solution of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid[(S)-3-azido-1-(2-methanesulfonyl-pyridin-4-yl)-propyl]-amide (86 mg, 0.17 mmol) in THF (7 mL) was added triphenylphosphine (57 mg, 0.22 mmol) (gas evolved) followed by water (700 μL). After 75 hours, the mixture was concentrated acetonitrile was added and the solution was filtered through a 0.45 um nylon Acrodisc and purified by reversed-phase HPLC using a 20 minute gradient of 5-95% MeCN (0.1% TFA) in H2O (0.1% TFA) (flow rate=25 mL/minute). The desired fractions were lyophilized to afford the title compound as a yellow solid.

Workup

  1. additionwas added
  2. filtrationthe solution was filtered through a 0.45 um nylon Acrodisc
  3. custompurified by reversed-phase
  4. waitHPLC using a 20 minute

Sources & evidence

ORD record
ord-388ff1e39196492cbd4f710f4b8ee381
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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