4-((Benzyl(methyl)amino)methyl)-2-((2,6-difluorobenzyl)(ethoxycarbonyl)amino)-5-(4-(3-methoxyureido)phenyl)thiophene-3-carboxylic acid → N-(4-(5-((benzyl(methyl)amino)methyl)-1-(2,6-difluorobenzyl)-3-(4-hydroxycyclohexyl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl)phenyl)-N'-methoxyurea

HRID 529187Notes

Reaction equation

HRID 529187 reaction equation
[CH2:1]([N:8]([CH2:10][C:11]1[C:12]([C:43](O)=[O:44])=[C:13]([N:28]([CH2:34][C:35]2[C:40]([F:41])=[CH:39][CH:38]=[CH:37][C:36]=2[F:42])[C:29](OCC)=[O:30])[S:14][C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]([NH:25][O:26][CH3:27])=[O:24])=[CH:18][CH:17]=1)[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:46][C@H:47]1[CH2:52][CH2:51][C@H:50]([OH:53])[CH2:49][CH2:48]1>>[CH2:1]([N:8]([CH2:10][C:11]1[C:12]2[C:43](=[O:44])[N:46]([CH:47]3[CH2:52][CH2:51][CH:50]([OH:53])[CH2:49][CH2:48]3)[C:29](=[O:30])[N:28]([CH2:34][C:35]3[C:40]([F:41])=[CH:39][CH:38]=[CH:37][C:36]=3[F:42])[C:13]=2[S:14][C:15]=1[C:16]1[CH:17]=[CH:18][C:19]([NH:22][C:23]([NH:25][O:26][CH3:27])=[O:24])=[CH:20][CH:21]=1)[CH3:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 183248004-((Benzyl(methyl)amino)methyl)-2-((2,6-difluorobenzyl)(ethoxycarbonyl)amino)-5-(4-(3-methoxyureido)phenyl)thiophene-3-carboxylic acidHCID 178511715HCID 178511715, compound

Product 1

HCID 59000838N-(4-(5-((benzyl(methyl)amino)methyl)-1-(2,6-difluorobenzyl)-3-(4-hydroxycyclohexyl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl)phenyl)-N'-methoxyureaYield 52.2%

Procedure

The similar reaction as described in Example 5 by using 4-(N-benzyl-N-methylaminomethyl)-2-[N-(2,6-difluorobenzyl)-N-ethoxycarbonylamino]-5-[4-(3-methoxyureido)phenyl]thiophene-3-carboxylic acid (3.19 g, 5 mmol) and trans-4-aminocyclohexanol (1.44 g, 12.5 mmol) gave the title compound (1.80 g, 52%) as colorless crystals.

Workup

  1. customThe similar reaction

Sources & evidence

ORD record
ord-361ed533c8a34b0292154b9452a4104a
Source dataset
uspto-grants-2016_05
Patent number
US09346822B2

Reaction notes

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