Potassium Carbonate → 2-(4-{2-[4-(2-Pyrrolidin-1-yl-ethoxy)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-5-yl}-pyrazol-1-yl)-ethanol

HRID 1472859Notes

Reaction equation

HRID 1472859 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[N:11]3[N:12]=[C:13]([NH:15][C:16]4[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][N:25]5[CH2:29][CH2:28][CH2:27][CH2:26]5)=[CH:18][CH:17]=4)[N:14]=[C:10]3[CH:9]=[CH:8][CH:7]=2)[CH:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].Cl[CH:37]([OH:39])[CH3:38]>CN(C)C=O>[N:25]1([CH2:24][CH2:23][O:22][C:19]2[CH:18]=[CH:17][C:16]([NH:15][C:13]3[N:14]=[C:10]4[CH:9]=[CH:8][CH:7]=[C:6]([C:4]5[CH:3]=[N:2][N:1]([CH2:38][CH2:37][OH:39])[CH:5]=5)[N:11]4[N:12]=3)=[CH:21][CH:20]=2)[CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 126390351-Chloroethan-1-olHCID 136146545[5-(1H-Pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine

Product 1

HCID 595895442-(4-{2-[4-(2-Pyrrolidin-1-yl-ethoxy)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-5-yl}-pyrazol-1-yl)-ethanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of [5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine (0.40 g, 1.03 mmol) in dimethylformamide (10 ml) was added potassium carbonate (2 g) followed by 1-chloroethanol (140 μl, 2.06 mmol). The mixture was stirred for 18 hours at room temperature, then filtered and concentrated in vacuo to provide a yellow solid. No further purification was required. Yield: 0.45 g, 89%; LCMS method: 2, RT: 2.10 min, MI: 434 [M+1].

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customto provide a yellow solid
  4. customNo further purification

Sources & evidence

ORD record
ord-0949391a152e47ebbe42e51200001eac
Source dataset
uspto-grants-2015_04
Patent number
US09012633B2

Reaction notes

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