HCID 58913148, compound → HCID 58913146, compound

HRID 1296580Notes

Reaction equation

HRID 1296580 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[N:17]2[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]2)[CH:10]=[C:9]1[S:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=[O:32])=[O:31])=O)(C)(C)C>C(O)(C)C.Cl>[C:33]1([S:30]([C:9]2[NH:8][C:16]3[C:11]([CH:10]=2)=[CH:12][CH:13]=[CH:14][C:15]=3[N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)(=[O:31])=[O:32])[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

4

Reactant 1

HCID 58913148HCID 58913148, compound

Product 1

HCID 58913146HCID 58913146, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3776IsopropanolSolvent

Procedure

A solution of 2-benzenesulfonyl-7-(4-tert-butoxycarbonyl-piperazin-1-yl)-indole-1-carboxylic acid tert butyl ester 1-4 (160 mg, 0.3 mmol) in isopropanol (15 mL) and concentrated HCl (4 mL) was refluxed for 1 hour. The reaction mixture was concentrated and the remaining powder was triturated with isopropanol (10 mL) and ether (20 mL). This was filtered to afford 2-benzenesulfonyl-7-piperazin-1-yl-1H-indole, Compound 1 of Table 1 as a white solid (90 mg, 89%). M+H=342.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe remaining powder was triturated with isopropanol (10 mL) and ether (20 mL)
  3. filtrationThis was filtered

Sources & evidence

ORD record
ord-0f44ebe451514f51909e4d7ba08d425b
Source dataset
uspto-grants-2007_07
Patent number
US07247651B2

Reaction notes

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