3,5-Dichlorobenzenesulfonyl chloride → 4-{4-Amino-5-[3-(3,5-dichloro-benzenesulfonylamino)-benzoyl]-pyrrolo[2,3-d]pyrimidin-7-yl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 916791

Reaction equation

HRID 916791 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9](Cl)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([N:26]2[C:30]3[N:31]=[CH:32][N:33]=[C:34]([NH2:35])[C:29]=3[C:28]([C:36](=[O:44])[C:37]3[CH:42]=[CH:41][CH:40]=[C:39]([NH2:43])[CH:38]=3)=[CH:27]2)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]>N1C=CC=CC=1>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([N:26]2[C:30]3[N:31]=[CH:32][N:33]=[C:34]([NH2:35])[C:29]=3[C:28]([C:36](=[O:44])[C:37]3[CH:42]=[CH:41][CH:40]=[C:39]([NH:43][S:9]([C:4]4[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=4)(=[O:11])=[O:10])[CH:38]=3)=[CH:27]2)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 5223883,5-Dichlorobenzenesulfonyl chlorideHCID 672197434-[4-Amino-5-(3-amino-benzoyl)-pyrrolo[2,3-d]pyrimidin-7-yl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 672193824-{4-Amino-5-[3-(3,5-dichloro-benzenesulfonylamino)-benzoyl]-pyrrolo[2,3-d]pyrimidin-7-yl}-piperidine-1-carboxylic acid tert-butyl esterYield 41%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3,5-Dichlorophenyl sulfonylchloride (2.8 g, 11.5 mmol) was added to a solution of 4-[4-amino-5-(3-amino-benzoyl)-pyrrolo[2,3-d]pyrimidin-7-yl]-piperidine-1-carboxylic acid tert-butyl ester (2.5 g, 5.7 mmol) in pyridine (55 mL). The reaction mixture was stirred at 40 C for 12 h in a sealed tube, quenched with H2O (45 mL), and extracted with EtOAc (3×50 mL). The combined organic extracts were washed with CuSO4 (3×150 mL), H2O (200 mL), and brine (200 mL) and dried (MgSO4), filtered, and concentrated in vacuo. The crude reaction mixture was filtered to obtain the titled compound as an off-white solid (1.5 g, 41%). MS: 646.5 (MH+); HPLC Rf: 6.95 min. (HPLC method 4); HPLC purity: 100%.

Workup

  1. customquenched with H2O (45 mL)
  2. extractionextracted with EtOAc (3×50 mL)
  3. washThe combined organic extracts were washed with CuSO4 (3×150 mL), H2O (200 mL), and brine (200 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude reaction mixture
  8. filtrationwas filtered

Sources & evidence

ORD record
ord-bbc8861be8454ac0a9df1dde1b1a3dbc
Source dataset
uspto-grants-2007_09
Patent number
US07271262B2

Linked notes

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