Water → HCID 59278376, compound

HRID 2198124Notes

Reaction equation

HRID 2198124 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-d1e1e45dba0848df8944f6bed63baf28
Source dataset
uspto-grants-2012_12
Patent number
US08338610B2

Reaction notes

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