Ammonium Hydroxide → HCID 68328593, compound

HRID 634214Notes

Reaction equation

HRID 634214 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([C:19]5[O:20][C:21]([NH:24][CH:25]([CH3:27])[CH3:26])=[N:22][N:23]=5)[CH:17]=4)[N:12]([S:28]([C:31]4[CH:37]=[CH:36][C:34]([CH3:35])=[CH:33][CH:32]=4)(=[O:30])=[O:29])[CH:11]=3)[N:7]=[C:6]([C:38](O)=[O:39])[CH:5]=2)[CH2:3][CH2:2]1.C[N:42](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH4+].[OH-]>CN(C=O)C>[CH:1]1([C:4]2[N:9]=[C:8]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([C:19]5[O:20][C:21]([NH:24][CH:25]([CH3:26])[CH3:27])=[N:22][N:23]=5)[CH:17]=4)[N:12]([S:28]([C:31]4[CH:32]=[CH:33][C:34]([CH3:35])=[CH:36][CH:37]=4)(=[O:29])=[O:30])[CH:11]=3)[N:7]=[C:6]([C:38]([NH2:42])=[O:39])[CH:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86725110HCID 86725110, compound

Product 1

HCID 68328593HCID 68328593, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Cyclopropyl-2-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1-tosyl-1H-indol-3-yl)pyrimidine-4-carboxylic acid (50 mg) was treated with HATU (51.1 mg, 0.134 mmol) followed by DMF (3 mL) and Hunig's base (0.1 mL). The reaction was stirred for 30 min at RT then treated with NH4OH (0.1 mL) and stirred for 30 min. The reaction was quenched with H2O and extracted with EtOAc (50 mL) and washed with brine (3×20 mL), dried over MgSO4, filtered and concentrated. The crude residue was used in the next step without further purification.

Workup

  1. stirringstirred for 30 min
  2. customThe reaction was quenched with H2O
  3. extractionextracted with EtOAc (50 mL)
  4. washwashed with brine (3×20 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was used in the next step without further purification

Sources & evidence

ORD record
ord-742b54c4de864557a013c7cb154b7bbb
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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