3-Methoxypropylamine → N-(3-methoxypropyl)thiophene-2-carboxamide
Reaction equation
C1(NC2N3N=CC(C=O)=C3N=C([C:16]3[S:20][C:19]([C:21](O)=[O:22])=[CH:18][CH:17]=3)C=2)CC1.CCN=C=NCCCN(C)C.CCN(CC)CC.C1C=CC2N(O)N=NC=2C=1.[CH3:52][O:53][CH2:54][CH2:55][CH2:56][NH2:57]>CN(C=O)C.C(OCC)(=O)C>[CH3:52][O:53][CH2:54][CH2:55][CH2:56][NH:57][C:21]([C:19]1[S:20][CH:16]=[CH:17][CH:18]=1)=[O:22]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
To 5-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)thiophene-2-carboxylic acid (30 mg, 0.091 mmol), EDCI (19 mg, 0.10 mmol), Et3N (14 μL, 0.10 mmol), and HOBt (14 mg, 0.10 mmol) in 2 mL of DMF pre-stirred for 5 minutes was added 3-methoxypropylamine (10 μL, 0.10 mmol). The reaction mixture was stirred at room temperature for 1 hour. The reaction was diluted with ethyl acetate, washed with H2O, brine, dried over MgSO4, filtered, and evaporated to dryness to provide 30 mg of 547-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)-N-(3-methoxypropyl)thiophene-2-carboxamide (83%). LCMS (M+1=400)
Workup
- washwashed with H2O, brine
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-24a2af6ed01c44058339869d6dbd1129
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08575177B2
Reaction notes
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