1-Chloro-2-(diethylamine)ethane hydrochloride → HCID 58923533, compound

HRID 1713664Notes

Reaction equation

HRID 1713664 reaction equation
CN(C)CCCOC1C=CC(C2SC(NC3C=CC=CC=3)=NC=2)=CC=1.[Br:26][C:27]1[CH:28]=[C:29]([C:33]2[S:37][C:36]([NH:38][C:39]3[CH:44]=[CH:43][C:42]([OH:45])=[CH:41][CH:40]=3)=[N:35][CH:34]=2)[CH:30]=[CH:31][CH:32]=1.Cl.Cl[CH2:48][CH2:49][N:50]([CH2:53][CH3:54])[CH2:51][CH3:52]>>[Br:26][C:27]1[CH:28]=[C:29]([C:33]2[S:37][C:36]([NH:38][C:39]3[CH:44]=[CH:43][C:42]([O:45][CH2:48][CH2:49][N:50]([CH2:53][CH3:54])[CH2:51][CH3:52])=[CH:41][CH:40]=3)=[N:35][CH:34]=2)[CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 3

HCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 11245147{5-[4-(3-Dimethylamino-propoxy)-phenyl]-thiazol-2-yl}phenyl-amineHCID 58923529HCID 58923529, compound

Product 1

HCID 58923533HCID 58923533, compound

Conditions

Temperature
70 °C

Procedure

The title compound is prepared as described in Example 8 for {5-[4-(3-dimethylamino-propoxy)-phenyl]-thiazol-2-yl}-phenyl-amine but starting from 4-[5-(3-bromo-phenyl)-thiazol-2-ylamino]-phenol and using (2-chloroethyl)-diethylamine hydrochloride. After stirring the reaction mixture for 30 min at 70° C., purification of the crude material by silica gel column chromatography (CH2Cl2/MeOH, 95/5 then 90/10) affords the title compound: ES-MS: 447.9 [M+2]+; single peak at tR=3.77 min (System 2); Rf=0.14 (CH2Cl2/MeOH, 90/10).

Workup

  1. customThe title compound is prepared
  2. custompurification of the crude material by silica gel column chromatography (CH2Cl2/MeOH, 95/5

Sources & evidence

ORD record
ord-1f0a85246b46456ab6f8f40e00bba02f
Source dataset
uspto-grants-2010_09
Patent number
US07795288B2

Reaction notes

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