Methanamine, hydrochloride (1:1) → HCID 117987705, compound

HRID 2206192Notes

Reaction equation

HRID 2206192 reaction equation
[Cl:1][C:2]1[C:3]2[N:12]([C:13]3[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=3[F:20])[N:11]=[C:10]([C:21]3[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=3)[C:4]=2[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[Cl-].C[NH3+].C[CH2:34][N:35]=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O.C(N(CC)CC)C>[Cl:1][C:2]1[C:3]2[N:12]([C:13]3[C:14]([F:20])=[CH:15][CH:16]=[CH:17][C:18]=3[F:19])[N:11]=[C:10]([C:21]3[CH:29]=[CH:28][C:24]([C:25]([NH:35][CH3:34])=[O:26])=[CH:23][CH:22]=3)[C:4]=2[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 11637Methanamine, hydrochloride (1:1)HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 117988151HCID 117988151, compound

Product 1

HCID 117987705HCID 117987705, compoundYield 89.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 4-(7-chloro-1-(2,6-difluorophenyl)-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)benzoic acid (78.3 mg) in anhydrous DMF (3 mL) were added methylammonium chloride (25.4 mg), EDCI hydrochloride (72.2 mg), HOBt (57.7 mg) and triethylamine (0.052 mL) at room temperature, and the mixture was stirred at room temperature for 96 hr. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (72.0 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-30e2b9b96a5e4c598e47f123ed2dfd10
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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