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3-Chloro-5-(5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-ylamino)phenol hydrochloride → 3-Chloro-5-[(7-{(2E)-4-[methyl(1-methylethyl)amino]but-2-enoyl}-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-yl)amino]phenol

HRID 38603
Notes
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Reaction equation

HRID 38603 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([OH:23])[CH:6]=[C:7]([NH:9][C:10]2[C:11]3[C:18]4[CH2:19][CH2:20][NH:21][CH2:22][C:17]=4[S:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:8]=1.Cl.[CH3:25][N:26]([CH:33]([CH3:35])[CH3:34])[CH2:27]/[CH:28]=[CH:29]/[C:30](O)=[O:31]>>[Cl:2][C:3]1[CH:4]=[C:5]([OH:23])[CH:6]=[C:7]([NH:9][C:10]2[C:11]3[C:18]4[CH2:19][CH2:20][N:21]([C:30](=[O:31])/[CH:29]=[CH:28]/[CH2:27][N:26]([CH3:25])[CH:33]([CH3:35])[CH3:34])[CH2:22][C:17]=4[S:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 668500883-Chloro-5-(5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-ylamino)phenol hydrochlorideHCID 86650197(2E)-4-[methyl(1-methylethyl)amino]but-2-enoic acid hydrochloride

Product 1

HCID 668497853-Chloro-5-[(7-{(2E)-4-[methyl(1-methylethyl)amino]but-2-enoyl}-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-yl)amino]phenol

Procedure

The title compound was prepared in analogy to Example 122 from 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 (2E)-4-[methyl(1-methylethyl)amino]but-2-enoic acid hydrochloride from Example 2A (73 mg, 0.38 mmol) to yield 24 mg (19%) as tan crystals.

Workup

  1. customto yield 24 mg (19%) as tan crystals

Sources & evidence

ORD record
ord-3242df423dd445a4876eb89e7d85304a
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08524722B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes