Diisopropylethylamine → (4-Methoxy-2-trifluoromethyl-phenyl)-(5-thiophen-3-yl-thiazol-2-yl)-amine

HRID 1713681Notes

Reaction equation

HRID 1713681 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2SC(NC3C=CC(O)=CC=3)=N[CH:7]=2)=[CH:2]1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH2:30])=[S:29])=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=1.NC(N)=S.CCN(C(C)C)C(C)C>C(Cl)Cl.CO>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]2[S:29][C:6]([C:3]3[CH:4]=[CH:5][S:1][CH:2]=3)=[CH:7][N:30]=2)=[C:23]([C:31]([F:34])([F:32])[F:33])[CH:22]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2723790ThioureaHCID 112888354-(5-Thiophen-3-yl-thiazol-2-yl-amino)-phenolHCID 58923517(4-Methoxy-2-trifluoromethyl-phenyl)-thiourea

Product 1

HCID 58923518(4-Methoxy-2-trifluoromethyl-phenyl)-(5-thiophen-3-yl-thiazol-2-yl)-amine

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
50 °C

Procedure

The title compound is prepared as described in Example 12 (Procedure B) for 4-(5-thiophen-3-yl-thiazol-2-yl-amino)-phenol but starting from (4-methoxy-2-trifluoromethyl-phenyl)-thiourea. After addition of the thiourea, the reaction mixture is heated to 50° C. for 30 min. The mixture is heated to 70° C. for 16 h, after addition of DIEA. The title compound: ES-MS: 357.0 [M+H]+; single peak at tR=4.36 min (System 2); Rf=0.56 (CH2Cl2/MeOH, 95/5).

Workup

  1. customThe title compound is prepared
  2. temperatureThe mixture is heated to 70° C. for 16 h

Sources & evidence

ORD record
ord-8b9cd22d79a7460ba0663620e20ac4ef
Source dataset
uspto-grants-2010_09
Patent number
US07795288B2

Reaction notes

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