4-Bromocrotonic acid → 3-({7-[(2E)-4-(3-Azabicyclo[3.2.1]oct-3-yl)but-2-enoyl]-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-yl}amino)-5-chlorophenol

HRID 38610Notes

Reaction equation

HRID 38610 reaction equation
Br[CH2:2]/[CH:3]=[CH:4]/[C:5]([OH:7])=O.Cl.[Cl:9][C:10]1[CH:11]=[C:12]([OH:30])[CH:13]=[C:14]([NH:16][C:17]2[C:18]3[C:25]4[CH2:26][CH2:27][NH:28][CH2:29][C:24]=4[S:23][C:19]=3[N:20]=[CH:21][N:22]=2)[CH:15]=1.[CH:31]12[CH2:38][CH:35]([CH2:36][CH2:37]1)[CH2:34][NH:33][CH2:32]2>>[CH:31]12[CH2:38][CH:35]([CH2:36][CH2:37]1)[CH2:34][N:33]([CH2:2]/[CH:3]=[CH:4]/[C:5]([N:28]1[CH2:27][CH2:26][C:25]3[C:18]4[C:17]([NH:16][C:14]5[CH:13]=[C:12]([OH:30])[CH:11]=[C:10]([Cl:9])[CH:15]=5)=[N:22][CH:21]=[N:20][C:19]=4[S:23][C:24]=3[CH2:29]1)=[O:7])[CH2:32]2

Participants

4

Reactant 3

HCID 64364114-Bromocrotonic acidHCID 123134903-Azabicyclo(3.2.1)octaneHCID 668500883-Chloro-5-(5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-ylamino)phenol hydrochloride

Product 1

HCID 581169863-({7-[(2E)-4-(3-Azabicyclo[3.2.1]oct-3-yl)but-2-enoyl]-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-yl}amino)-5-chlorophenol

Procedure

In analogy to Example 130, the title compound was prepared from (2E)-4-bromobut-2-enoic acid (84 mg, 0.41 mmol), 3-chloro-5-(5,6,7,8-tetrahydropyrido[4′,3′:4,5]thieno[2,3-d]pyrimidin-4-ylamino)phenol hydrochloride from Example 65A (100 mg, 0.27 mmol) and 3-azabicyclo[3.2.1]-octane (48 mg, 0.43 mmol) to yield 44 mg (32%).

Workup

  1. customto yield 44 mg (32%)

Sources & evidence

ORD record
ord-71f2dfca2daa430a9dc6165096dd2899
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Reaction notes

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