1-Methyloctahydropyrrolo[3,4-B]pyrrole → N-(3,4-Dichlorophenyl)-7-[(2E)-4-(1-methylhexahydropyrrolo[3,4-b]pyrrol-5(1H)-yl)but-2-enoyl]-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-amine

HRID 38577Notes

Reaction equation

HRID 38577 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].[CH3:29][N:30]1[CH2:34][CH2:33][CH:32]2[CH2:35][NH:36][CH2:37][CH:31]12>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:36]5[CH2:35][CH:32]6[CH:31]([N:30]([CH3:29])[CH2:34][CH2:33]6)[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 150700011-Methyloctahydropyrrolo[3,4-B]pyrroleHCID 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 25221096N-(3,4-Dichlorophenyl)-7-[(2E)-4-(1-methylhexahydropyrrolo[3,4-b]pyrrol-5(1H)-yl)but-2-enoyl]-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-amine

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-methyloctahydropyrrolo[3,4-b]pyrrole (41 mg, 0.32 mmol), and the mixture was stirred at rt for 20 h. After purification by preparative HPLC, the title compound was crystallized from dichloromethane/petroleum ether to yield 12 mg (14%).

Workup

  1. customAfter purification by preparative HPLC
  2. customthe title compound was crystallized from dichloromethane/petroleum ether
  3. customto yield 12 mg (14%)

Sources & evidence

ORD record
ord-a14a4ad9a7004c14a67e6b4d582d85c8
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Reaction notes

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