Pyridine → HCID 57934844, compound

HRID 1433145Notes

Reaction equation

HRID 1433145 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:25]2[C:26]([C:30]3[CH:35]=[C:34]([Cl:36])[C:33]([O:37][CH2:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)=[CH:32][C:31]=3[O:45][CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)=[N:27][NH:28][CH:29]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].N1C=CC=CC=1>ClCCl>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:25]2[C:26]([C:30]3[CH:35]=[C:34]([Cl:36])[C:33]([O:37][CH2:38][C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)=[CH:32][C:31]=3[O:45][CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)=[N:27][N:28]([S:7]([C:4]3[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=3)(=[O:9])=[O:8])[CH:29]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 178452255HCID 178452255, compound

Product 1

HCID 57934844HCID 57934844, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Para toluene sulphonyl chloride (180 mg, )0.95 mmol) was added to a stirred solution of 4-[3-(2,4-Bis-benzyloxy-5-chloro-phenyl)-1H-pyrazol-4-yl]-piperazine-1-carboxylic acid tert-butyl ester (500 mg, 0.9 mmol) in dichloromethane (10 ml) and pyridine (0.9 mmol). Stirring was continued for 18 h, then the solution was partitioned between water (20 ml) and ethyl acetate (2×20 ml). The combined organic phases were dried over magnesium sulphate, and concentrated in vacuo to leave a yellow oil. Purfication on silica (20 g) eluting with hexane, followed by hexane:diethyl ether, 1:1, then diethyl ether gave 4-[3-(2,4-Bis-benzyloxy-5-chloro-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrazol-4-yl]-piperazine-1-carboxylic acid tert-butyl ester (490 mg, 77%)

Workup

  1. customthe solution was partitioned between water (20 ml) and ethyl acetate (2×20 ml)
  2. dry with materialThe combined organic phases were dried over magnesium sulphate
  3. concentrationconcentrated in vacuo
  4. customto leave a yellow oil
  5. washPurfication on silica (20 g) eluting with hexane

Sources & evidence

ORD record
ord-6b1eee9a74754f07ab50b87bab1f8140
Source dataset
uspto-grants-2009_11
Patent number
US07612201B2

Reaction notes

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