4-chloro-2-(1-(5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one → HCID 178425440, compound

HRID 715487Notes

Reaction equation

HRID 715487 reaction equation
Cl[C:2]1[C:7]2[CH2:8][N:9]([CH:12]([C:14]3[CH:15]=[N:16][C:17]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[C:18]([CH3:20])[CH:19]=3)[CH3:13])[C:10](=[O:11])[C:6]=2[CH:5]=[CH:4][N:3]=1.C[Si](C)(C)CCOC[N:33]1[CH:37]=[CH:36][C:35]([C:38]([NH2:40])=[O:39])=[N:34]1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH3:20][C:18]1[CH:19]=[C:14]([CH:12]([N:9]2[C:10](=[O:11])[C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:40][C:38]([C:35]4[CH:36]=[CH:37][NH:33][N:34]=4)=[O:39])[C:7]=3[CH2:8]2)[CH3:13])[CH:15]=[N:16][C:17]=1[O:21][CH2:22][C:23]([F:26])([F:25])[F:24]

Participants

4

Reactant 2

HCID 898749364-chloro-2-(1-(5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-oneHCID 898754771-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole-3-carboxamide

Product 1

HCID 178425440HCID 178425440, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

The reaction is carried out in a similar manner to Example-1 (Method-A) using 4-chloro-2-(1-(5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one (50 mg, 0.13 mmol, Intermediate-2, single enantiomer) and 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole-3-carboxamide (63 mg, 0.26 mmol). The obtained crude is diluted with DCM/TFA (1:1, 2 mL), and the mixture is stirred at rt for 1 h. Then, the solvent is removed in vacuo, and the residue is purified by preparative LC-MS to give 6.3 mg (11% yield) of the title compound.

Workup

  1. customThe obtained crude
  2. customThen, the solvent is removed in vacuo
  3. customthe residue is purified by preparative LC-MS

Sources & evidence

ORD record
ord-9bc4006b347e482fa8871624be5051ab
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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