Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 59020065, compound

HRID 971157Notes

Reaction equation

HRID 971157 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[C:14](=[O:30])[N:15]([C:18]4[CH:23]=[CH:22][C:21]([C:24]5([C:27](O)=[O:28])[CH2:26][CH2:25]5)=[CH:20][CH:19]=4)[CH2:16][CH2:17][C:12]=3[C:11]([C:31]([F:34])([F:33])[F:32])=[N:10]2)=[CH:5][CH:4]=1.Cl.[CH3:36][NH:37][O:38][CH3:39].CCN(C(C)C)C(C)C.Cl.CN(C)CCCN=C=NCC>CN(C=O)C.CCOC(C)=O>[CH3:39][O:38][N:37]([CH3:36])[C:27]([C:24]1([C:21]2[CH:20]=[CH:19][C:18]([N:15]3[CH2:16][CH2:17][C:12]4[C:11]([C:31]([F:34])([F:33])[F:32])=[N:10][N:9]([C:6]5[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=5)[C:13]=4[C:14]3=[O:30])=[CH:23][CH:22]=2)[CH2:26][CH2:25]1)=[O:28]

Participants

7

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 695159871-{4-[l-(4-Methoxy-phenyl)-7-oxo-3-trifluoromethyl-1,4,5,7-tetrahydro-pyrazolo[3,4-c]pyridin-6-yl]-phenyl}cyclopropane carboxylic acid

Product 1

HCID 59020065HCID 59020065, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-{4-[1-(4-Methoxy-phenyl)-7-oxo-3-trifluoromethyl-1,4,5,7-tetrahydro-pyrazolo[3,4-c]pyridin-6-yl]-phenyl}cyclopropane carboxylic acid (1.12 g, 2.37 mmol) and N,O-dimethylhydroxylamine hydrochloride (0.255 g, 2.61 mmol) were dissolved in DMF (20.0 mL) and DIEA (2.0 mL, 11.5 mmol) was added dropwise. 1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.54 g, 2.8 mmol) was added and the reaction was allowed to proceed under nitrogen at rt for 12 h. The reaction was diluted with EtOAc, washed 1N HCl, brine, dried over Na2SO4, filtered and concentrated. The reaction was purified via flash chromatography (silica, 100% EtOAc, then 10% MeOH/CH2Cl2) to give the title compound. LC/MS (ESI+) 515.6 (M+H).

Workup

  1. washwashed 1N HCl, brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe reaction was purified via flash chromatography (silica, 100% EtOAc

Sources & evidence

ORD record
ord-4ef35135ee1544ac90f9307d2db883e5
Source dataset
uspto-grants-2007_12
Patent number
US07312214B2

Reaction notes

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