Ammonia → 4-cyclopropyl-2-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1-tosyl-1H-indol-3-yl)pyrimidine-5-carboxamide

HRID 634309Notes

Reaction equation

HRID 634309 reaction equation
[CH:1]1([C:4]2[C:9]([C:10](O)=[O:11])=[CH:8][N:7]=[C:6]([C:13]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([C:22]5[O:23][C:24]([NH:27][CH:28]([CH3:30])[CH3:29])=[N:25][N:26]=5)[CH:20]=4)[N:15]([S:31]([C:34]4[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=4)(=[O:33])=[O:32])[CH:14]=3)[N:5]=2)[CH2:3][CH2:2]1.C1C[N:44]([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.O1CCOCC1.N>CN(C=O)C>[CH:1]1([C:4]2[C:9]([C:10]([NH2:44])=[O:11])=[CH:8][N:7]=[C:6]([C:13]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([C:22]5[O:23][C:24]([NH:27][CH:28]([CH3:29])[CH3:30])=[N:25][N:26]=5)[CH:20]=4)[N:15]([S:31]([C:34]4[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=4)(=[O:33])=[O:32])[CH:14]=3)[N:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 312751,4-Dioxane2×HCID 2724699PyBOPHCID 683286994-cyclopropyl-2-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1-tosyl-1H-indol-3-yl)pyrimidine-5-carboxylic acid

Product 1

HCID 683283234-cyclopropyl-2-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1-tosyl-1H-indol-3-yl)pyrimidine-5-carboxamideYield 243.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Cyclopropyl-2-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1-tosyl-1H-indol-3-yl)pyrimidine-5-carboxylic acid (107 mg, 0.192 mmol) was treated with PyBOP (169 mg, 0.326 mmol) and 1,4-dioxane (5 mL) and DMF (1.0 mL) and stirred at RT for 10 min. The reaction was then cooled in an ice bath and treated with NH3, 0.5 M solution in 1,4-dioxane (1.9 mL, 0.96 mmol) and stirred at 0° C. for 1.5 h. The reaction was quenched with water, extracted with EtOAc (25 mL), washed with brine (2×25 mL), dried over MgSO4, filtered and concentrated affording 261 mg of the crude amide. MS (ESI, pos. ion) m/z: 558.2 (M+H)+. The crude material was used without further purification.

Workup

  1. temperatureThe reaction was then cooled in an ice bath
  2. stirringstirred at 0° C. for 1.5 h
  3. customThe reaction was quenched with water
  4. extractionextracted with EtOAc (25 mL)
  5. washwashed with brine (2×25 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-509ffe2291d5415cb78c772a0663c337
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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