Ammonia → 5-(1-(4-chlorophenyl)-1-(4-(methylsulfonamido)-1H-indazol-1-yl)propyl)-1,2,4-oxadiazole-3-carboxamide

HRID 1477900Notes

Reaction equation

HRID 1477900 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]([O:32]CC)=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.[NH3:35]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:25]2[O:29][N:28]=[C:27]([C:30]([NH2:35])=[O:32])[N:26]=2)([N:11]2[C:19]3[C:14](=[C:15]([NH:20][S:21]([CH3:24])(=[O:22])=[O:23])[CH:16]=[CH:17][CH:18]=3)[CH:13]=[N:12]2)[CH2:9][CH3:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 70563586ethyl 5-(1-(4-chlorophenyl)-1-(4-(methylsulfonamido)-1H-indazol-1-yl)propyl)-1,2,4-oxadiazole-3-carboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from Step E above (0.015 g, 0.030 mmol) was dissolved in a 7 N solution of ammonia in methanol (2.6 mL). After stirring at RT for 45 min, the resulting mixture was concentrated under reduced pressure. The residue was dissolved in dioxane/water, acidified with TFA, and purified directly on RP-HPLC to give the title compound. LC/MS m/z=475.0[M+H]+. 1H NMR (500 MHz, CD3OD): δ (ppm) 8.34 (s, 1H), 7.43 (d, J=8.8 Hz, 2H), 7.37 (d, J=8.8 Hz, 2H), 7.16-7.14 (m, 2H); 6.48-6.45 (m, 1H), 3.20-3.12 (m, 1H), 3.14-3.05 (m, 1H), 3.04 (s, 3H), 0.89 (t, J=7.4 Hz, 3H).

Workup

  1. concentrationthe resulting mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in dioxane/water
  3. custompurified directly on RP-HPLC

Sources & evidence

ORD record
ord-3304a8513693495798d78699eb8adec5
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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