4-Bromocrotonic acid → 5-({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)-2,3-dichlorophenol

HRID 38613Notes

Reaction equation

HRID 38613 reaction equation
Cl.[Cl:2][C:3]1[C:8]([Cl:9])=[CH:7][C:6]([NH:10][C:11]2[C:12]3[C:19]4[CH2:20][CH2:21][NH:22][CH2:23][C:18]=4[S:17][C:13]=3[N:14]=[CH:15][N:16]=2)=[CH:5][C:4]=1[OH:24].Br[CH2:26]/[CH:27]=[CH:28]/[C:29]([OH:31])=O.[CH:32]12[CH2:39][CH:36]([CH2:37][CH2:38]1)[CH2:35][NH:34][CH2:33]2>>[CH:32]12[CH2:39][CH:36]([CH2:37][CH2:38]1)[CH2:35][N:34]([CH2:26]/[CH:27]=[CH:28]/[C:29]([N:22]1[CH2:21][CH2:20][C:19]3[C:12]4[C:11]([NH:10][C:6]5[CH:7]=[C:8]([Cl:9])[C:3]([Cl:2])=[C:4]([OH:24])[CH:5]=5)=[N:16][CH:15]=[N:14][C:13]=4[S:17][C:18]=3[CH2:23]1)=[O:31])[CH2:33]2

Participants

4

Reactant 3

HCID 64364114-Bromocrotonic acidHCID 123134903-Azabicyclo(3.2.1)octaneHCID 668498872,3-Dichloro-5-(5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-ylamino)phenol hydrochloride

Product 1

HCID 252209945-({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)-2,3-dichlorophenol

Procedure

The compound was synthesized in analogy to Example 147 from 2,3-dichloro-5-(5,6,7,8-tetrahydropyrido[4′,3′:4,5]thieno[2,3-d]pyrimidin-4-ylamino)phenol hydrochloride from Example 69A (100 mg, 0.25 mmol), (2E)-4-bromobut-2-enoic acid (61 mg, 0.37 mmol) and 3-azabicyclo[3.2.1]-octane (44 mg, 0.40 mmol) to yield 25 mg (19%).

Workup

  1. customto yield 25 mg (19%)

Sources & evidence

ORD record
ord-7a225c26fde0489bbfdbd09aedc4ba93
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Reaction notes

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