Dimethylformamide → 4-[2-(2,4-Dichloro-phenoxy)-phenylsulfamoyl]-N-{2-oxo-2-[4-(2-pyrrolidin-1-yl-ethyl)-piperazin-1-yl]-ethyl}-benzamide

HRID 446859Notes

Reaction equation

HRID 446859 reaction equation
[Cl:1][C:2]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][S:12]([C:15]1[CH:27]=[CH:26][C:18]([C:19]([NH:21][CH2:22][C:23](O)=[O:24])=[O:20])=[CH:17][CH:16]=1)(=[O:14])=[O:13].[CH3:33][N:34]([CH3:37])[CH:35]=O.[CH3:38][N:39](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)[CH3:40].F[P-](F)(F)(F)(F)F.[CH2:62]([N:64]([CH2:67][CH3:68])[CH2:65]C)[CH3:63]>ClCCl>[Cl:1][C:2]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][S:12]([C:15]1[CH:16]=[CH:17][C:18]([C:19]([NH:21][CH2:22][C:23](=[O:24])[N:39]2[CH2:40][CH2:35][N:34]([CH2:37][CH2:65][N:64]3[CH2:67][CH2:68][CH2:63][CH2:62]3)[CH2:33][CH2:38]2)=[O:20])=[CH:26][CH:27]=1)(=[O:14])=[O:13]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68493493{4-[2-(2,4-Dichloro-phenoxy)-phenylsulfamoyl]-benzoylamino}-acetic acid

Product 1

HCID 248127564-[2-(2,4-Dichloro-phenoxy)-phenylsulfamoyl]-N-{2-oxo-2-[4-(2-pyrrolidin-1-yl-ethyl)-piperazin-1-yl]-ethyl}-benzamideYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of {4-[2-(2,4-dichloro-phenoxy)-phenylsulfamoyl]-benzoylamino}-acetic acid (42 mg, 0.085 mmol) in a mixture of dichloromethane (2 mL) and dimethylformamide (0.2 mL) 1-(2-pyrrolidin-1-yl-ethyl)-piperazine (EMKA-Chemie) (18 mg, 0.1 mmol), HBTU (46 mg, 0.12 mmol) and triethylamine (60 μL, 0.4 mmol) were added. The mixture was stirred at room temperature for 24 h, then purified by column chromatography using Kieselgel 60 (0.015-0.040 mm) as adsorbent (Merck) and gradient elution starting with 100% A eluent and processing to a mixture of 70% A and 30% B eluent over a period of 15 minutes (eluent A: chloroform; eluent B: methanol containing 5% of ammonium hydroxide) to yield 45.8 mg (82%) of the title compound. MS (EI) 661.2 (MH+).

Workup

  1. additionwere added
  2. custompurified by column chromatography
  3. washas adsorbent (Merck) and gradient elution
  4. additionstarting with 100% A eluent and processing to a mixture of 70% A and 30% B eluent over a period of 15 minutes (eluent A: chloroform; eluent B: methanol containing 5% of ammonium hydroxide)

Sources & evidence

ORD record
ord-2e4ea148cb0e4562b3b4e03d1ad23298
Source dataset
uspto-grants-2013_07
Patent number
US08481527B2

Reaction notes

Loading…