[4-(Benzo[b]thiophen-2-yl)-pyrimidin-2-yl]-[3-(4-methylpiperazin-1-yl)-propyl]-amine → [4-(6-Bromobenzo[b]thiophen-2-yl)-5-chloropyrimidin-2-yl]-[3-(4-methylpiperazin-1-yl)-propyl]-amine tri-hydrochloride

HRID 1986295Notes

Reaction equation

HRID 1986295 reaction equation
S1C(C2C=CN=C([NH:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]3)N=2)=CC2C=CC=CC1=2.[Br:27][C:28]1[CH:29]=[CH:30][C:31]2[CH:35]=[C:34]([C:36]3[C:41]([Cl:42])=[CH:40][N:39]=[C:38](Cl)[N:37]=3)[S:33][C:32]=2[CH:44]=1>>[ClH:42].[ClH:42].[ClH:42].[Br:27][C:28]1[CH:29]=[CH:30][C:31]2[CH:35]=[C:34]([C:36]3[C:41]([Cl:42])=[CH:40][N:39]=[C:38]([NH:12][CH2:13][CH2:14][CH2:15][N:16]4[CH2:17][CH2:18][N:19]([CH3:22])[CH2:20][CH2:21]4)[N:37]=3)[S:33][C:32]=2[CH:44]=1

Participants

3

Reactant 2

HCID 57720607[4-(Benzo[b]thiophen-2-yl)-pyrimidin-2-yl]-[3-(4-methylpiperazin-1-yl)-propyl]-amineHCID 866253874-(6-Bromobenzo[b]thiophen-2-yl)-2,5-dichloropyrimidine

Product 1

HCID 68902280[4-(6-Bromobenzo[b]thiophen-2-yl)-5-chloropyrimidin-2-yl]-[3-(4-methylpiperazin-1-yl)-propyl]-amine tri-hydrochloride

Procedure

Using the method of [4-(benzo[b]thiophen-2-yl)-pyrimidin-2-yl]-[3-(4-methylpiperazin-1-yl)-propyl]-amine, the title compound is synthesized from 4-(6-bromobenzo[b]thiophen-2-yl)-2,5-dichloropyrimidine and isolated as a light orange solid. ES+(m/z) 480 (35C1, 79Br), 482 ([37Cl, 79Br] and [35Cl, 81Br]) and 484 (37Cl, 81Br) [M(free base)+H].

Workup

  1. customisolated as a light orange solid

Sources & evidence

ORD record
ord-4fa83df309c04a618103a4f4e9e10832
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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