Phosphorus oxychloride → N-(1-(1-(4-chlorophenyl)-1-(3-cyano-1,2,4-oxadiazol-5-yl)propyl)-1H-indazol-4-yl)methane sulfonamide

HRID 1477901Notes

Reaction equation

HRID 1477901 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:25]2[O:29][N:28]=[C:27]([C:30]([NH2:32])=O)[N:26]=2)([N:11]2[C:19]3[C:14](=[C:15]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH:16]=[CH:17][CH:18]=3)[CH:13]=[N:12]2)[CH2:9][CH3:10])=[CH:4][CH:3]=1.O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:11]2[C:19]3[C:14](=[C:15]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH:16]=[CH:17][CH:18]=3)[CH:13]=[N:12]2)([C:25]2[O:29][N:28]=[C:27]([C:30]#[N:32])[N:26]=2)[CH2:9][CH3:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 705639165-(1-(4-chlorophenyl)-1-(4-(methylsulfonamido)-1H-indazol-1-yl)propyl)-1,2,4-oxadiazole-3-carboxamide

Product 1

HCID 70562427N-(1-(1-(4-chlorophenyl)-1-(3-cyano-1,2,4-oxadiazol-5-yl)propyl)-1H-indazol-4-yl)methane sulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of the product from Example 37 step F above (6.8 mg, 0.014 mmol) in pyridine (1.0 mL) was added POCl3 (32.8 mg, 0.28 mmol) at 0° C. After stirring at RT overnight, the reaction mixture was concentrated under reduced pressure. The resulting residue was diluted with dioxane/water, acidified with TFA, and purified directly on RP-HPLC to give the title compound. LC/MS m/z=457.1 [M+H]+.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionThe resulting residue was diluted with dioxane/water
  3. custompurified directly on RP-HPLC

Sources & evidence

ORD record
ord-802f4e6636db401d9be7c029d224ef9b
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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