Triphenylphosphine → HCID 59370349, compound

HRID 661704Notes

Reaction equation

HRID 661704 reaction equation
[Cl:1][C:2]1[C:19]([C:20]2[CH:21]=[N:22][C:23]([C:28]([F:31])([F:30])[F:29])=[CH:24][C:25]=2[C:26]#[N:27])=[CH:18][C:5]([C:6]([N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])[CH3:9])=[O:7])=[C:4]([OH:32])[CH:3]=1.[O:33]1[CH:37]=[C:36]([CH2:38][CH2:39][CH2:40]O)[CH:35]=[N:34]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Cl:1][C:2]1[C:19]([C:20]2[CH:21]=[N:22][C:23]([C:28]([F:29])([F:30])[F:31])=[CH:24][C:25]=2[C:26]#[N:27])=[CH:18][C:5]([C:6]([N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])[CH3:9])=[O:7])=[C:4]([O:32][CH2:40][CH2:39][CH2:38][C:36]2[CH:35]=[N:34][O:33][CH:37]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 197396173-(1,2-Oxazol-4-yl)propan-1-olHCID 68603614HCID 68603614, compound

Product 1

HCID 59370349HCID 59370349, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-hydroxy-N-(2-methoxy-phenyl)-N-methyl-benzamide (30 mg, 0.065 mmol) in THF (700 μL), 3-isoxazol-4-yl-propan-1-ol (9 mg, 0.071 mmol), triphenylphosphine (26 mg, 0.089 mmol) and DIAD (20 μL, 0.098 mmol) were added. The mixture was stirred at rt overnight, concentrated, diluted with 1 mL MeOH and purified by prep HPLC to give 4-chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-(3-isoxazol-4-yl-propoxy)-N-(2-methoxyphenyl)-N-methyl-benzamide 46-1. MS: 571.2 (M+H)+, tR=6.12 min (method 3).

Workup

  1. concentrationconcentrated
  2. additiondiluted with 1 mL MeOH
  3. custompurified by prep HPLC

Sources & evidence

ORD record
ord-4b054211a383477dbfd56ba4b81f1d7f
Source dataset
uspto-grants-2011_12
Patent number
US08084614B2

Reaction notes

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