Toluene → N-[3-({2-[(cyclopropylcarbonyl)amino]-1,3-benzothiazol-6-yl}oxy)phenyl]-3-(trifluoromethyl)benzamide

HRID 2190365Notes

Reaction equation

HRID 2190365 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O.S(Cl)(Cl)=O.C1(C)C=CC=CC=1.[NH2:25][C:26]1[CH:27]=[C:28]([CH:45]=[CH:46][CH:47]=1)[O:29][C:30]1[CH:44]=[CH:43][C:33]2[N:34]=[C:35]([NH:37][C:38]([CH:40]3[CH2:42][CH2:41]3)=[O:39])[S:36][C:32]=2[CH:31]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH:40]1([C:38]([NH:37][C:35]2[S:36][C:32]3[CH:31]=[C:30]([O:29][C:28]4[CH:27]=[C:26]([NH:25][C:6](=[O:8])[C:5]5[CH:9]=[CH:10][CH:11]=[C:3]([C:2]([F:1])([F:13])[F:12])[CH:4]=5)[CH:47]=[CH:46][CH:45]=4)[CH:44]=[CH:43][C:33]=3[N:34]=2)=[O:39])[CH2:41][CH2:42]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 99633-(Trifluoromethyl)benzoic acidHCID 24386Thionyl ChlorideHCID 86655349N-[6-(3-aminophenoxy)-1,3-benzothiazol-2-yl]cyclopropanecarboxamide

Product 1

HCID 58349040N-[3-({2-[(cyclopropylcarbonyl)amino]-1,3-benzothiazol-6-yl}oxy)phenyl]-3-(trifluoromethyl)benzamideYield 76.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Using 3-(trifluoromethyl)benzoic acid (182 mg, 959 μmol), thionyl chloride (0.4 mL, 5.48 mmol), toluene (5 mL), N-[6-(3-aminophenoxy)-1,3-benzothiazol-2-yl]cyclopropanecarboxamide (129 mg, 395 μmol) produced in Example A1(vii), pyridine (5 mL), and N,N-dimethylpyridine-4-amine (21.3 mg, 176.0 μmol) as starting materials, and in the same manner as in Example A1(viii), the title compound (150 mg, 76%) was obtained as a colorless amorphous substance.

Sources & evidence

ORD record
ord-89c8651b66784b73b67c907b52ecb444
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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