3-Methoxypropylamine → N-[2-(3-cyano-1H-indol-5-yl)-ethyl]-4-[2-(3-methoxy-propylamino)-pyrimidin-4-yl]-benzamide

HRID 1264294Notes

Reaction equation

HRID 1264294 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH2:6].[C:7]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][CH2:19][NH:20][C:21](=[O:35])[C:22]3[CH:27]=[CH:26][C:25]([C:28]4[CH:33]=[CH:32][N:31]=[C:30](Cl)[N:29]=4)=[CH:24][CH:23]=3)[CH:16]=2)[NH:11][CH:10]=1)#[N:8]>>[C:7]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][CH2:19][NH:20][C:21](=[O:35])[C:22]3[CH:27]=[CH:26][C:25]([C:28]4[CH:33]=[CH:32][N:31]=[C:30]([NH:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])[N:29]=4)=[CH:24][CH:23]=3)[CH:16]=2)[NH:11][CH:10]=1)#[N:8]

Participants

3

Reactant 2

HCID 16723-MethoxypropylamineHCID 18617562N-[2-(3-Cyano-1H-indol-5-yl)-ethyl]-4-[2-chloropyrimidin-4-yl]benzamide

Product 1

HCID 18617853N-[2-(3-cyano-1H-indol-5-yl)-ethyl]-4-[2-(3-methoxy-propylamino)-pyrimidin-4-yl]-benzamide

Procedure

Using 3-methoxy-propylamine and N-[2-(3-Cyano-1H-indol-5-yl)-ethyl]-4-[2-chloro-pyrimidin-4-yl]-benzamide (reference example 1az) as substrates. 1H NMR (DMSO) δ 1.81 (m, 2H); 2.98 (m, 2H); 3.24 (s, 3H); 3.41 (m, 4H); 3.56 (m, 2H); 7.19 (m, 2H); 7.28 (bs, 1H); 7.50 (m, 2H); 7.92 (m, 2H); 8.18 (m, 3H); 8.38 (bs, 1H); 8.68 (bs, 1H); 12.13 (bs, 1H). MS (ion spray) m/z 455 (M+H)+.

Sources & evidence

ORD record
ord-74bd67d67d0d44e28be4b742b71c40d4
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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