[5-(4-Methoxy-phenyl)-thiazol-2-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine → [5-(4-Methoxy-phenyl)-thiazol-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine

HRID 1713639Notes

Reaction equation

HRID 1713639 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18](OCCN4CCCC4)=[CH:17][CH:16]=3)=[N:11][CH:10]=2)=[CH:5][CH:4]=1.[CH3:29][N:30]1[CH2:35][CH2:34][N:33](C2C=CC(NC(N)=S)=CC=2)[CH2:32][CH2:31]1>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[S:13][C:12]([NH:14][C:15]3[CH:16]=[CH:17][C:18]([N:33]4[CH2:34][CH2:35][N:30]([CH3:29])[CH2:31][CH2:32]4)=[CH:19][CH:20]=3)=[N:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 11188635[5-(4-Methoxy-phenyl)-thiazol-2-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amineHCID 39146979[4-(4-Methylpiperazin-1-yl)phenyl]thiourea

Product 1

HCID 11773416[5-(4-Methoxy-phenyl)-thiazol-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine

Procedure

The title compound is prepared as described in Example 3 for [5-(4-methoxy-phenyl)-thiazol-2-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine but using [4-(4-methyl-piperazin-1-yl)-phenyl]-thiourea. Purification of the crude product by silica gel (20 g) column chromatography (CH2Cl2/MeOH, 90/10) and subsequent washing of the purified product with MeOH affords the title compound as a light beige solid: ES-MS: 381.0 [M+H]+; single peak at tR=6.13 min (System 1); Rf=0.53 (CH2Cl2/MeOH, 80/20).

Workup

  1. customThe title compound is prepared
  2. customPurification of the crude product by silica gel (20 g) column chromatography (CH2Cl2/MeOH, 90/10)
  3. washsubsequent washing of the purified product with MeOH

Sources & evidence

ORD record
ord-b2d2e76060e14a2caed39a8b6f4863bc
Source dataset
uspto-grants-2010_09
Patent number
US07795288B2

Reaction notes

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