Benzoyl chloride → HCID 67074466, compound

HRID 336862Notes

Reaction equation

HRID 336862 reaction equation
[C:1]([N:5]1[C:9]2=[N:10][C:11]([C:35]3[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][C:36]=3[F:42])=[C:12]([C:33]#[N:34])[C:13]([C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]4)=[CH:16][CH:15]=3)=[C:8]2[C:7]([CH3:43])=[N:6]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:51](Cl)(=[O:58])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1>ClCCl>[C:51]([O:41][C:38]1[CH:39]=[CH:40][C:35]([C:11]2[N:10]=[C:9]3[N:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[N:6]=[C:7]([CH3:43])[C:8]3=[C:13]([C:14]3[CH:15]=[CH:16][C:17]([N:20]4[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH2:25]4)=[CH:18][CH:19]=3)[C:12]=2[C:33]#[N:34])=[C:36]([F:42])[CH:37]=1)(=[O:58])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 136353000HCID 136353000, compound

Product 1

HCID 67074466HCID 67074466, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.33 g (0.56 mmol) of tert-butyl 4-(4-(1-tert-butyl-5-cyano-6-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-yl)phenyl)piperazine-1-carboxylate and 325 μL (0.24 g, 2.3 mmol) of triethylamine in 17 ml of anhydrous dichloromethane are added dropwise 78 μL (0.09 g, 0.67 mmol) of benzoyl chloride. The mixture is stirred at room temperature for 24 h. The mixture is diluted with dichloromethane and washed with water. The aqueous phase is then extracted with dichloromethane. The organic phases are combined, dried over sodium sulfate, and concentrated to give 0.38 g (quantitative) of tert-butyl 4-(4-(6-(4-(benzoyloxy)-2-fluorophenyl)-1-tert-butyl-5-cyano-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-yl)phenyl)piperazine-1-carboxylate which is used in the following step without purification.

Workup

  1. washwashed with water
  2. extractionThe aqueous phase is then extracted with dichloromethane
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-443caa5a05244d5891adeb3d1dd7ca7b
Source dataset
uspto-grants-2014_11
Patent number
US08889711B2

Reaction notes

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