Potassium Carbonate → HCID 178504708, compound

HRID 966466Notes

Reaction equation

HRID 966466 reaction equation
C([O-])([O-])=O.[K+].[K+].[F:7][C:8]1[CH:15]=[CH:14][C:13]([NH:16][CH:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[S:35]([CH3:38])(=[O:37])=[O:36])=[CH:25][C:24]=3[F:39])[C:18]2=[O:40])=[CH:12][C:9]=1[C:10]#[N:11].C[N:42](C=O)C.[OH2:46]>O>[F:7][C:8]1[CH:15]=[CH:14][C:13]([NH:16][CH:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[S:35]([CH3:38])(=[O:37])=[O:36])=[CH:25][C:24]=3[F:39])[C:18]2=[O:40])=[CH:12][C:9]=1[C:10]([NH:42][OH:46])=[NH:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21962138N,N-Dimethylformamide--water (1/1)HCID 691435262-Fluoro-5-[1-(3-fluoro-2'-methanesulfonyl-biphenyl-4-yl)-2-oxo-piperidin-3-ylamino]-benzonitrile

Product 1

HCID 178504708HCID 178504708, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of acetoxyhydroamic acid (27 mg, 2.5eq) and K2CO3 (98 mg, 5eq) in DMF/H2O (3:1, 4 ml) was stirred at room temperature for 20 min. To this mixture was added 2-fluoro-5-[1-(3-fluoro-2′-methanesulfonyl-biphenyl-4-yl)-2-oxo-piperidin-3-ylamino]-benzonitrile (68 mg, 0.141 mmol) prepared as described under Ex. 58a above. The whole was stirred and heated at 110° C. for 18 h. The mixture was diluted with water and extracted 3× with EtOAc. The combined organic extracts were washed with brine, dried over MgSO4, filtered and evaporated. Purification by reverse phase HPLC yielded the title compound (50 mg, 72%) 1H NMR (DMSO-d6) δ 8.11 (1H,d,J=8 Hz), 7.79 (1H,t,J=7, 3 Hz), 7.71 (1H,t,J=7, 73 Hz), 7.46 (2H,m), 7.37 (1H,d,J=11 Hz), 7.28 (1H,d,J=8 Hz), 7.18 (1H,t,J=9.5 Hz), 6.98 (1H,m), 6.85 (1H,m), 4.29 (1H,m), 3.72 (2H,t,J=6.2 Hz), 2.91 (3H,s), 2.28 (1H,m), 2.08 (2H,m), 1.84 (1H,m). MS 515.3 (M+H)+.

Workup

  1. customprepared
  2. stirringThe whole was stirred
  3. temperatureheated at 110° C. for 18 h
  4. extractionextracted 3× with EtOAc
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customPurification by reverse phase HPLC

Sources & evidence

ORD record
ord-660857a2a1ed4ba09b41ee441c93c161
Source dataset
uspto-grants-2005_10
Patent number
US06951872B2

Reaction notes

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