Potassium Carbonate → HCID 58674484, compound

HRID 1994149Notes

Reaction equation

HRID 1994149 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[C:10]([O:12][C:13]2[CH:14]=[C:15]([CH2:19][CH2:20][C:21]([NH:23][C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([C:31]([F:34])([F:33])[F:32])[CH:25]=3)=[O:22])[CH:16]=[CH:17][CH:18]=2)[CH:9]=[CH:8][N:7]=1)=[O:4].[CH2:35]([N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1)[CH3:36].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([NH:23][C:21](=[O:22])[CH2:20][CH2:19][C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([O:12][C:10]3[CH:9]=[CH:8][N:7]=[C:6]([NH:5][C:3](=[O:4])[CH2:2][N:40]4[CH2:41][CH2:42][N:37]([CH2:35][CH3:36])[CH2:38][CH2:39]4)[CH:11]=3)[CH:14]=2)=[CH:25][C:26]=1[C:31]([F:32])([F:33])[F:34]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 791961-EthylpiperazineHCID 58674579HCID 58674579, compound

Product 1

HCID 58674484HCID 58674484, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-[3-({2-[(chloroacetyl)amino]pyridin-4-yl}oxy)phenyl]-N-[4-chloro-3-(trifluoromethyl)phenyl]-propanamide (0.050 g, 0.090 mmol), 1-ethylpiperazine (0.040 mL, 0.29 mmol), and K2CO3 (0.050 g, 0.36 mmol) was stirred at 60° C. in DMF for 1 h. The mixture was concentrated and partitioned between EtOAc and water. The organic solution was concentrated and the residue was purified by column chromatography to give A-192. 1H NMR (400 MHz, d6-DMSO) δ: 10.98 (m, 1H), 10.60 (m, 1H), 8.21 (m, 2H), 7.83 (dd, 1H), 7.63 (d, 1H), 7.60 (m, 1H), 7.41 (t, 1H), 7.21 (d, 1H), 7.10 (m, 1H), 7.01 (m, 1H), 6.75 (dd, 1H), 4.85 (br, 6H), 3.84 (br, 1H), 3.39 (br, 1H), 3.22 (br, 2H), 3.13 (m, 2H), 2.95 (t, 2H), 2.70 (t, 2H), and 1.23 (t, 3H). LCMS: (FA) ES+ 590.3 (M+1).

Workup

  1. concentrationThe mixture was concentrated
  2. custompartitioned between EtOAc and water
  3. concentrationThe organic solution was concentrated
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-de33b06698634eae9630ded285df7563
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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