{5-[4-(3-Dimethylamino-propoxy)-phenyl]-thiazol-2-yl}phenyl-amine → [5-(2-Chloro-phenyl)-thiazol-2-yl]-[4-(2-diethylamino-ethoxy)-phenyl]-amine

HRID 1713667Notes

Reaction equation

HRID 1713667 reaction equation
CN(C)CCCO[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:17][C:16]([NH:18][C:19]3[CH:24]=[CH:23]C=[CH:21][CH:20]=3)=[N:15][CH:14]=2)=[CH:9][CH:8]=1.ClC1C=CC=CC=1C1S[C:36]([NH:38][C:39]2[CH:44]=CC(O)=CC=2)=NC=1.[ClH:46].Cl[CH2:48][CH2:49]N(C)C.[CH2:53](Cl)Cl.[CH3:56][OH:57]>>[Cl:46][C:9]1[CH:8]=[CH:7][CH:12]=[CH:11][C:10]=1[C:13]1[S:17][C:16]([NH:18][C:19]2[CH:20]=[CH:21][C:56]([O:57][CH2:48][CH2:49][N:38]([CH2:36][CH3:53])[CH2:39][CH3:44])=[CH:23][CH:24]=2)=[N:15][CH:14]=1

Participants

5

Reactant 4

HCID 11245147{5-[4-(3-Dimethylamino-propoxy)-phenyl]-thiazol-2-yl}phenyl-amineHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 21226129Dichloromethane methanolHCID 589235284-[5-(2-Chloro-phenyl)-thiazol-2-ylamino]-phenol

Product 1

HCID 86613640[5-(2-Chloro-phenyl)-thiazol-2-yl]-[4-(2-diethylamino-ethoxy)-phenyl]-amine

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-(2-chloro-phenyl)-thiazol-2-ylamino]-phenol and using (2-chloroethyl)-dimethylamine hydrochloride. The title compound: ES-MS: 374.0 [M+H]+; single peak at tR=3.17 min (System 2); Rf=0.23 (CH2Cl2/MeOH, 90/10).

Workup

  1. customThe title compound is prepared

Sources & evidence

ORD record
ord-5a0afbb972d646aaa505c484b06125b3
Source dataset
uspto-grants-2010_09
Patent number
US07795288B2

Reaction notes

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