3-Methoxypropylamine → 5-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)-N-(3-methoxypropyl)thiophene-2-carboxamide

HRID 624752Notes

Reaction equation

HRID 624752 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](O)=[O:22])=[CH:18][CH:17]=3)[CH:6]=2)[CH2:3][CH2:2]1.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>[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]([NH:57][CH2:56][CH2:55][CH2:54][O:53][CH3:52])=[O:22])=[CH:18][CH:17]=3)[CH:6]=2)[CH2:2][CH2:3]1

Participants

8

Reactant 5

HCID 16723-MethoxypropylamineHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 583142305-(7-(Cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)thiophene-2-carboxylic acid

Product 1

HCID 583137435-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)-N-(3-methoxypropyl)thiophene-2-carboxamideYield 83%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

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 5-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-yl)-N-(3-methoxypropyl)thiophene-2-carboxamide (83%). LCMS (M+1=400)

Workup

  1. washwashed with H2O, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-41760d48d3234fcea773e8df2a56d012
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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