Water → HCID 59507059, compound

HRID 1800508Notes

Reaction equation

HRID 1800508 reaction equation
[F:1][C:2]([F:16])([O:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=O)[CH:3]([F:5])[F:4].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[NH2:41][C:42]1[CH:43]=[CH:44][C:45]([CH3:64])=[C:46]([CH:63]=1)[O:47][C:48]1[N:53]=[C:52]2[S:54][C:55]([NH:57][C:58]([CH:60]3[CH2:62][CH2:61]3)=[O:59])=[N:56][C:51]2=[CH:50][CH:49]=1.O>N1C=CC=CC=1>[CH:60]1([C:58]([NH:57][C:55]2[S:54][C:52]3[C:51]([N:56]=2)=[CH:50][CH:49]=[C:48]([O:47][C:46]2[CH:63]=[C:42]([NH:41][C:10](=[O:12])[C:9]4[CH:13]=[CH:14][CH:15]=[C:7]([O:6][C:2]([F:1])([F:16])[CH:3]([F:4])[F:5])[CH:8]=4)[CH:43]=[CH:44][C:45]=2[CH3:64])[N:53]=3)=[O:59])[CH2:61][CH2:62]1

Participants

6

Reactant 4

HCID 962WaterHCID 5786803-(1,1,2,2-Tetrafluoroethoxy)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 59507059HCID 59507059, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-(1,1,2,2-tetrafluoroethoxy)benzoic acid (44 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 precipitate was collected by filtration, washed with water and ethyl acetate, and dried to give the title compound (55 mg, 56%) as a colorless 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 precipitate was collected by filtration
  5. washwashed with water and ethyl acetate
  6. customdried

Sources & evidence

ORD record
ord-9afbb5edb39a44308f7418eb2d25402e
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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