Water → HCID 57964982, compound

HRID 1931728Notes

Reaction equation

HRID 1931728 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].[CH3:14][C:15]1[C:20]([O:21][C:22]2[N:27]=[CH:26][N:25]=[C:24]3[N:28]([CH:31]4[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]4)[N:29]=[CH:30][C:23]=23)=[CH:19][CH:18]=[CH:17][N:16]=1.C(N(C(C)C)CC)(C)C.O>ClCCl>[N+:11]([C:8]1[CH:9]=[CH:10][C:5]([O:4][C:2]([N:34]2[CH2:33][CH2:32][CH:31]([N:28]3[C:24]4=[N:25][CH:26]=[N:27][C:22]([O:21][C:20]5[C:15]([CH3:14])=[N:16][CH:17]=[CH:18][CH:19]=5)=[C:23]4[CH:30]=[N:29]3)[CH2:36][CH2:35]2)=[O:3])=[CH:6][CH:7]=1)([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 57544435HCID 57544435, compound2×

Product 1

HCID 57964982HCID 57964982, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Nitrophenyl chloroformate (Aldrich Chemical Company, Inc., Milwaukee, Wis., USA 268 mg, 1.33 mmol) was added in three portions to a cooled (˜0° C.) solution of 4-(2-methyl-pyridin-3-yloxy)-1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine (Intermediate 28; 275 mg, 0.89 mmol), and diisopropylethylamine (390 μL, 2.2 mmol) in anhydrous dichloromethane (10 mL). The mixture was warmed to room temperature and stirred for 1 h. Water (10 mL) was added, the layers were separated and the organic layer was washed with brine, dried (sodium sulfate), filtered, evaporated, and purified on a 23 g Supelco column, eluting with 0-7% methanol/dichloromethane to give 4-[4-(2-methyl-pyridin-3-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid 4-nitro-phenyl ester (180 mg, 43%) as a white foam.

Workup

  1. customthe layers were separated
  2. washthe organic layer was washed with brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. customevaporated
  6. custompurified on a 23 g Supelco column
  7. washeluting with 0-7% methanol/dichloromethane

Sources & evidence

ORD record
ord-b6529d0f4a0245fca7b9eeebe9836cbb
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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