4-Amino-5-(chloromethyl)-2-methylpyrimidine → 1'-({1-[(4-Amino-2-methylpyrimidin-5-yl)methyl]-6-chloro-1H-indol-3-yl}carbonyl)-5-fluoro-3H-spiro[2-benzofuran-1,4'-piperidin]-3-one

HRID 1865969Notes

Reaction equation

HRID 1865969 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([N:13]3[CH2:18][CH2:17][C:16]4([C:22]5[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:21]=5[C:20](=[O:28])[O:19]4)[CH2:15][CH2:14]3)=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.Cl[CH2:30][C:31]1[C:32]([NH2:38])=[N:33][C:34]([CH3:37])=[N:35][CH:36]=1>>[NH2:38][C:32]1[C:31]([CH2:30][N:8]2[C:9]3[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:10]=3)[C:6]([C:11]([N:13]3[CH2:18][CH2:17][C:16]4([C:22]5[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:21]=5[C:20](=[O:28])[O:19]4)[CH2:15][CH2:14]3)=[O:12])=[CH:7]2)=[CH:36][N:35]=[C:34]([CH3:37])[N:33]=1

Participants

3

Reactant 2

HCID 4212454-Amino-5-(chloromethyl)-2-methylpyrimidineHCID 596576231'-[(6-chloro-1H-indol-3-yl)carbonyl]-5-fluoro-3H-spiro[2-benzofuran-1,4'-piperidin]-3-one

Product 1

HCID 596576731'-({1-[(4-Amino-2-methylpyrimidin-5-yl)methyl]-6-chloro-1H-indol-3-yl}carbonyl)-5-fluoro-3H-spiro[2-benzofuran-1,4'-piperidin]-3-one

Procedure

Following the general procedure III as described above, the alkylation of 1′-[(6-chloro-1H-indol-3-yl)carbonyl]-5-fluoro-3H-spiro[2-benzofuran-1,4′-piperidin]-3-one (prepared according to example 19 above) with 5-chloromethyl-2-methyl-pyrimidin-4-ylamine (described in Pharmaceutical Chemistry Journal (Translation of Khimiko-Farmatsevticheskii Zhurnal) (1999), 33(2), 101-103) gave the title compound.

Sources & evidence

ORD record
ord-1174403c110f4db190937ff6ecf2909b
Source dataset
uspto-grants-2009_12
Patent number
US07629353B2

Reaction notes

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