Ammonia → HCID 53374891, compound

HRID 532286Notes

Reaction equation

HRID 532286 reaction equation
[CH3:1][C:2]1[C:10]2[C:9]([NH:11][C:12]3[C:13]([O:18][CH:19]([CH3:24])[C:20]([F:23])([F:22])[F:21])=[N:14][CH:15]=[CH:16][CH:17]=3)=[N:8][CH:7]=[N:6][C:5]=2[S:4][C:3]=1[C:25](O)=[O:26].C[N:29](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.N>CN(C=O)C.O1CCOCC1>[CH3:1][C:2]1[C:10]2[C:9]([NH:11][C:12]3[C:13]([O:18][CH:19]([CH3:24])[C:20]([F:21])([F:22])[F:23])=[N:14][CH:15]=[CH:16][CH:17]=3)=[N:8][CH:7]=[N:6][C:5]=2[S:4][C:3]=1[C:25]([NH2:29])=[O:26]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 53374892HCID 53374892, compound

Product 1

HCID 53374891HCID 53374891, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

5-Methyl-4-(2-(1,1,1-trifluoropropan-2yloxy)pyridin-3-ylamino)thieno[2,3-d]pyrimidine-6-carboxylic acid (278 mg), HATU (320 mg) and Hünig's Base (144 μl) were dissolved in DMF (6.5 ml) at 0° C. The reaction was stirred for 30 minutes after this time NH3 in dioxane (0.5 M; 5.3 ml) was added. The reaction was allowed to warm to room temperature overnight. The reaction mixture was concentrated in vacuo. The residue was extracted with dichloromethane and water. The organic layer was separated, dried and evaporated. The crude product was purified by chromatography (silica/dichloromethane: methanol: NH3 90:10:1).

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. extractionThe residue was extracted with dichloromethane and water
  4. customThe organic layer was separated
  5. customdried
  6. customevaporated
  7. customThe crude product was purified by chromatography (silica/dichloromethane: methanol: NH3 90:10:1)

Sources & evidence

ORD record
ord-9587113636e04ce8bd93d7c6216aab2c
Source dataset
uspto-grants-2014_10
Patent number
US08853193B2

Reaction notes

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