Ammonium Chloride → 5-(7-(Cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)thiophene-2-carboxamide
Reaction equation
[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][C:13]([CH:14]=[O:15])=[C:9]3[N:8]=[C:7]([C:16]3[S:20][C:19]([C:21]([OH:23])=O)=[CH:18][CH:17]=3)[CH:6]=2)[CH2:3][CH2:2]1.C[N:25](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[Cl-].[NH4+]>CN(C=O)C.C(OCC)(=O)C>[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][C:13]([CH:14]=[O:15])=[C:9]3[N:8]=[C:7]([C:16]3[S:20][C:19]([C:21]([NH2:25])=[O:23])=[CH:18][CH:17]=3)[CH:6]=2)[CH2:2][CH2:3]1Participants
8
Reactant 5
HCID 25517Ammonium Chloride
HCID 757711-Hydroxybenzotriazole
HCID 81531Diisopropylethylamine
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 583142305-(7-(Cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)thiophene-2-carboxylic acidProduct 1
Reagents, catalysts & solvents 2
Procedure
To 5-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)thiophene-2-carboxylic acid (40 mg, 0.122 mmol), HATU (70 mg, 0.183 mmol), HOBt (4 mg, 0.024 mmol) and DIEA (85 μL, 0.488 mmol) in 2 mL of DMF was added ammonium chloride (20 mg, 0.366 mmol). The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate washed with saturated NaHCO3 solution, brine, dried over MgSO4, filtered, and evaporated to dryness to provide 42 mg of 5-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)thiophene-2-carboxamide (100%). LCMS (M+1=328).
Workup
- washwashed with saturated NaHCO3 solution, brine
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-b4837c29dedc42d3b51d9132d1867a95
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09303033B2
Reaction notes
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