1-(2-Pyridyl)piperazine → N-(3,4-Dichlorophenyl)-7-[(2E)-4-(4-pyridin-2-ylpiperazin-1-yl)but-2-enoyl]-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-amine

HRID 38576

Reaction equation

HRID 38576 reaction equation
Cl[CH2:2]/[CH:3]=[CH:4]/[C:5]([N:7]1[CH2:28][CH2:27][C:10]2[C:11]3[C:16]([NH:17][C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=4)=[N:15][CH:14]=[N:13][C:12]=3[S:26][C:9]=2[CH2:8]1)=[O:6].[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1>CN(C=O)C>[Cl:25][C:20]1[CH:19]=[C:18]([NH:17][C:16]2[C:11]3[C:10]4[CH2:27][CH2:28][N:7]([C:5](=[O:6])/[CH:4]=[CH:3]/[CH2:2][N:38]5[CH2:39][CH2:40][N:35]([C:30]6[CH:31]=[CH:32][CH:33]=[CH:34][N:29]=6)[CH2:36][CH2:37]5)[CH2:8][C:9]=4[S:26][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:23]=[CH:22][C:21]=1[Cl:24]

Participants

4

Reactant 2

HCID 944591-(2-Pyridyl)piperazineHCID 581168067-[(2E)-4-Chlorobut-2-enoyl]-N-(3,4-dichlorophenyl)-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-amine

Product 1

HCID 25221097N-(3,4-Dichlorophenyl)-7-[(2E)-4-(4-pyridin-2-ylpiperazin-1-yl)but-2-enoyl]-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-amineYield 79.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of Example 59A (80 mg, 0.16 mmol) in DMF (1 mL) was added 1-pyridin-2-ylpiperazine (52 mg, 0.32 mmol), and the mixture was stirred at rt for 3 h and then heated to 50° C. for 4 h. After purification by preparative HPLC, the product crystallized upon trituration with dichloromethane to yield 74 mg (79%) of the title compound.

Workup

  1. temperatureheated to 50° C. for 4 h
  2. customAfter purification by preparative HPLC
  3. customthe product crystallized upon trituration with dichloromethane

Sources & evidence

ORD record
ord-8b0cbf93ec1948008fc11b3cfa0b0809
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Linked notes

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