Triethylamine → N-methoxy-N-methyl-5-pyrrolidin-1-yl-7-(tetrahydro-2H-pyran-4-ylamino)pyrazolo[1,5-a]pyrimidine-2-carboxamide

HRID 869716Notes

Reaction equation

HRID 869716 reaction equation
[N:1]1([C:6]2[CH:11]=[C:10]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[N:9]3[N:19]=[C:20]([C:22]([OH:24])=O)[CH:21]=[C:8]3[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.C(N=C=NCCCN(C)C)C.Cl.[CH3:38][NH:39][O:40][CH3:41].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:41][O:40][N:39]([CH3:38])[C:22]([C:20]1[CH:21]=[C:8]2[N:7]=[C:6]([N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH:11]=[C:10]([NH:12][CH:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)[N:9]2[N:19]=1)=[O:24]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 674075435-pyrrolidin-1-yl-7-(tetrahydro-2H-pyran-4-ylamino)pyrazolo[1,5-a]pyrimidine-2-carboxylic acid

Product 1

HCID 86674519N-methoxy-N-methyl-5-pyrrolidin-1-yl-7-(tetrahydro-2H-pyran-4-ylamino)pyrazolo[1,5-a]pyrimidine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-pyrrolidin-1-yl-7-(tetrahydro-2H-pyran-4-ylamino)pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (2.15 g, 5.26 mmol) in dichloromethane (60 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.27 g, 13.0 mmol), N,O-dimethylhydroxylamine hydrochloride (2.49 g, 13.0 mmol), and triethylamine (2.30 g, 22.7 mmol) at 0° C. After being stirred for 17 h at room temperature, the reaction mixture was poured into saturated sodium bicarbonate. The mixture was extracted with chloroform. The organic layer was washed with brine, dried over sodium sulfate, filtrated and concentrated in vacuo. The crude was purified by silica gel column chromatography (chloroform to chloroform:methanol=19:1) to give N-methoxy-N-methyl-5-pyrrolidin-1-yl-7-(tetrahydro-2H-pyran-4-ylamino)pyrazolo[1,5-a]pyrimidine-2-carboxamide. MS (APCI): m/z 375 (M+H).

Workup

  1. extractionThe mixture was extracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo
  6. customThe crude was purified by silica gel column chromatography (chloroform to chloroform:methanol=19:1)

Sources & evidence

ORD record
ord-f60e5036c27d4171abcb2bb1e82cb41c
Source dataset
uspto-grants-2015_03
Patent number
US08969376B2

Reaction notes

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