2-Amino-5-fluoropyridine → N-(4-(5-((benzyl(methyl)amino)methyl)-1-(2,6-difluorobenzyl)-3-(5-fluoropyridin-2-yl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl)phenyl)-N'-methoxyurea

HRID 1594175Notes

Reaction equation

HRID 1594175 reaction equation
C(N(C[CH2:11][C:12]1[C:13]([C:44](O)=[O:45])=[C:14]([N:29]([CH2:35][C:36]2[C:41]([F:42])=[CH:40][CH:39]=[CH:38][C:37]=2[F:43])[C:30](OCC)=[O:31])[S:15][C:16]=1[C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:26][O:27][CH3:28])=[O:25])=[CH:19][CH:18]=1)C)C1C=CC=CC=1.[NH2:47][C:48]1[CH:53]=[CH:52][C:51]([F:54])=[CH:50][N:49]=1>>[CH2:35]([N:29]([CH2:11][C:12]1[C:13]2[C:44](=[O:45])[N:47]([C:48]3[CH:53]=[CH:52][C:51]([F:54])=[CH:50][N:49]=3)[C:30](=[O:31])[N:29]([CH2:35][C:36]3[C:37]([F:43])=[CH:38][CH:39]=[CH:40][C:41]=3[F:42])[C:14]=2[S:15][C:16]=1[C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:26][O:27][CH3:28])=[O:25])=[CH:19][CH:18]=1)[CH3:14])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

3

Reactant 2

HCID 27377012-Amino-5-fluoropyridineHCID 867605814-(N-benzyl-N-methylaminoethyl)-2-(N-(2,6-difluorobenzyl)-N-ethoxycarbonylamino)-5-(4-(3-methoxyureido)phenyl)thiophene-3-carboxylic acid

Product 1

HCID 86620015N-(4-(5-((benzyl(methyl)amino)methyl)-1-(2,6-difluorobenzyl)-3-(5-fluoropyridin-2-yl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl)phenyl)-N'-methoxyureaYield 63.1%

Procedure

The similar reaction as described in Example 5 by using 4-(N-benzyl-N-methylaminoethyl)-2-(N-(2,6-difluorobenzyl)-N-ethoxycarbonylamino)-5-(4-(3-methoxyureido)phenyl)thiophene-3-carboxylic acid (10.0 g, 15.65 mmol) and 2-amino-5-fluoropyridine (3.51 g, 31.30 mmol) gave N-(4-(5-((benzyl(methyl)amino)methyl)-1-(2,6-difluorobenzyl)-3-(5-fluoropyridin-2-yl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl)phenyl)-N′-methoxyurea (3.39 g, 32%) as white solids. The similar reaction as described in Reference Example 18 by using the compound (1.0 g, 1.46 mmol) gave the title compound (560 mg, 64%) as white solids.

Workup

  1. customThe similar reaction

Sources & evidence

ORD record
ord-f889bdf4b77044409b5ffd5604934cb8
Source dataset
uspto-grants-2007_11
Patent number
US07300935B2

Reaction notes

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