Water → N-[3-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-4-methylphenyl]-3-(trifluoromethoxy)benzamide

HRID 1800507Notes

Reaction equation

HRID 1800507 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=O.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[NH2:39][C:40]1[CH:41]=[CH:42][C:43]([CH3:62])=[C:44]([CH:61]=1)[O:45][C:46]1[N:51]=[C:50]2[S:52][C:53]([NH:55][C:56]([CH:58]3[CH2:60][CH2:59]3)=[O:57])=[N:54][C:49]2=[CH:48][CH:47]=1.O>N1C=CC=CC=1>[CH:58]1([C:56]([NH:55][C:53]2[S:52][C:50]3[C:49]([N:54]=2)=[CH:48][CH:47]=[C:46]([O:45][C:44]2[CH:61]=[C:40]([NH:39][C:7](=[O:9])[C:6]4[CH:10]=[CH:11][CH:12]=[C:4]([O:3][C:2]([F:1])([F:14])[F:13])[CH:5]=4)[CH:41]=[CH:42][C:43]=2[CH3:62])[N:51]=3)=[O:57])[CH2:59][CH2:60]1

Participants

6

Reactant 4

HCID 962WaterHCID 660963-(Trifluoromethoxy)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58451281HCID 58451281, compound

Product 1

HCID 59506998N-[3-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-4-methylphenyl]-3-(trifluoromethoxy)benzamideYield 52.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-(trifluoromethoxy)benzoic acid (37.5 mg, 0.185 mmol) in pyridine (2.0 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (70 mg, 0.185 mmol), and the mixture was stirred at room temperature for 10 min. N-[5-(5-Amino-2-methylphenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]cyclopropanecarboxamide (60 mg, 0.176 mmol) produced in Example C47(i) was added to the obtained solution, and the mixture was stirred at 70° C. for 20 hr. After the reaction mixture was cooled to room temperature, water (2 mL) was added, and the obtained yellow precipitate was collected by filtration, washed with water and ethyl acetate, and dried to give the title compound (48.5 mg, 52%) as a yellow powder.

Workup

  1. additionwas added to the obtained solution
  2. stirringthe mixture was stirred at 70° C. for 20 hr
  3. temperatureAfter the reaction mixture was cooled to room temperature
  4. filtrationthe obtained yellow precipitate was collected by filtration
  5. washwashed with water and ethyl acetate
  6. customdried

Sources & evidence

ORD record
ord-647e96c32eca478f89e8b9f966fbaba1
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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