Triethylamine → (4-Difluoromethoxy-phenyl)-{4-[1-(2-fluoro-4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidin-1-yl}-methanone

HRID 719464

Reaction equation

HRID 719464 reaction equation
[F:1][CH:2]([F:13])[O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[F:39][C:40]1[CH:45]=[C:44]([S:46]([CH3:49])(=[O:48])=[O:47])[CH:43]=[CH:42][C:41]=1[N:50]1[C:54]2=[N:55][CH:56]=[N:57][C:58]([O:59][CH:60]3[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]3)=[C:53]2[CH:52]=[N:51]1.C(N(CC)CC)C>CN(C=O)C>[F:13][CH:2]([F:1])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:63]2[CH2:64][CH2:65][CH:60]([O:59][C:58]3[N:57]=[CH:56][N:55]=[C:54]4[N:50]([C:41]5[CH:42]=[CH:43][C:44]([S:46]([CH3:49])(=[O:48])=[O:47])=[CH:45][C:40]=5[F:39])[N:51]=[CH:52][C:53]=34)[CH2:61][CH2:62]2)=[O:10])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 7373604-(Difluoromethoxy)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 218977401-(2-Fluoro-4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine hydrochloride

Product 1

HCID 21897847(4-Difluoromethoxy-phenyl)-{4-[1-(2-fluoro-4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidin-1-yl}-methanoneYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Difluoromethoxy-benzoic acid (527 mg, 2.8 mmol) and HATU (1.06 g, 2.8 mmol) were stirred together in DMF at room temperature for 30 min. 1-(2-Fluoro-4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine hydrochloride (800 mg, 1.87 mmol) and triethylamine (785 μL, 5.61 mmol) were added next. The resulting mixture was allowed to stir for 24 hours. Progress of the reaction was monitored by TLC and LCMS. Removal of organic solvents in vacuo and purification by HPLC afforded Compound A193 as a beige solid (127 mg, 32%). Exact mass calculated for C25H22F2N5O5S 561.53, found 562.2 (MH+)

Workup

  1. customRemoval of organic solvents
  2. customin vacuo and purification by HPLC

Sources & evidence

ORD record
ord-3a36577a3f0e4078b5b5c04aef34e512
Source dataset
uspto-grants-2006_11
Patent number
US07132426B2

Linked notes

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