Flt-3 Inhibitor III → [4-(4-Methyl-piperazin-1-yl)-phenyl]-[5-(3-thiophen-3-yl-phenyl)-thiazol-2-yl]-amine

HRID 1713670Notes

Reaction equation

HRID 1713670 reaction equation
C1(C2SC(NC3C=CC(OCCN4CCCC4)=CC=3)=NC=2)C=CC=CC=1.[S:27]1[CH:31]=[CH:30][C:29]([C:32]2[CH:33]=[C:34]([CH2:38][CH:39]=O)[CH:35]=[CH:36][CH:37]=2)=[CH:28]1.[CH3:41][N:42]1[CH2:47][CH2:46][N:45]([C:48]2[CH:53]=[CH:52][C:51]([NH:54][C:55]([NH2:57])=[S:56])=[CH:50][CH:49]=2)[CH2:44][CH2:43]1>>[CH3:41][N:42]1[CH2:47][CH2:46][N:45]([C:48]2[CH:49]=[CH:50][C:51]([NH:54][C:55]3[S:56][C:38]([C:34]4[CH:35]=[CH:36][CH:37]=[C:32]([C:29]5[CH:30]=[CH:31][S:27][CH:28]=5)[CH:33]=4)=[CH:39][N:57]=3)=[CH:52][CH:53]=2)[CH2:44][CH2:43]1

Participants

4

Reactant 3

HCID 11772958Flt-3 Inhibitor IIIHCID 39146979[4-(4-Methylpiperazin-1-yl)phenyl]thioureaHCID 58923511(3-Thiophen-3-yl-phenyl)-acetaldehyde

Product 1

HCID 58923522[4-(4-Methyl-piperazin-1-yl)-phenyl]-[5-(3-thiophen-3-yl-phenyl)-thiazol-2-yl]-amine

Procedure

The title compound is prepared as described in Example 1 for (5-phenyl-thiazol-2-yl)-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine but using (3-thiophen-3-yl-phenyl)-acetaldehyde and [4-(4-methyl-piperazin-1-yl)-phenyl]-thiourea (Example 5). MPLC (CH3CN/H2O/TFA) purification affords the title compound: ES-MS: 435.0 [M+3]+; single peak at tR=3.09 min (System 2); Rf=0.25 (CH2Cl2/MeOH, 90/10).

Workup

  1. customThe title compound is prepared
  2. customMPLC (CH3CN/H2O/TFA) purification

Sources & evidence

ORD record
ord-d730815b85634a6db9a8b14b4e2d31f9
Source dataset
uspto-grants-2010_09
Patent number
US07795288B2

Reaction notes

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