1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 4-(4-((4'-Chloro(1,1'-biphenyl)-2-yl)methyl)-1-piperazinyl)-N-((4-(((1R)-3-(dimethylamino)-1-((phenylthio)methyl)propyl)amino)-3-nitrophenyl)sulfonyl)benzamide

HRID 661349Notes

Reaction equation

HRID 661349 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][N:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)=[CH:4][CH:3]=1.[CH3:30][N:31]([CH3:57])[CH2:32][CH2:33][C@@H:34]([NH:43][C:44]1[CH:49]=[CH:48][C:47]([S:50]([NH2:53])(=[O:52])=[O:51])=[CH:46][C:45]=1[N+:54]([O-:56])=[O:55])[CH2:35][S:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][N:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:22]=[CH:23][C:24]([C:25]([NH:53][S:50]([C:47]4[CH:48]=[CH:49][C:44]([NH:43][C@@H:34]([CH2:35][S:36][C:37]5[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=5)[CH2:33][CH2:32][N:31]([CH3:30])[CH3:57])=[C:45]([N+:54]([O-:56])=[O:55])[CH:46]=4)(=[O:51])=[O:52])=[O:26])=[CH:28][CH:29]=3)[CH2:17][CH2:16]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11502754(R)-4-((4-(Dimethylamino)-1-(phenylthio)butan-2-yl)amino)-3-nitrobenzenesulfonamideHCID 534349854-[4-(4'-Chlorobiphenyl-2-ylmethyl)piperazin-1-YL]benzoic acid

Product 1

HCID 112281834-(4-((4'-Chloro(1,1'-biphenyl)-2-yl)methyl)-1-piperazinyl)-N-((4-(((1R)-3-(dimethylamino)-1-((phenylthio)methyl)propyl)amino)-3-nitrophenyl)sulfonyl)benzamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of EXAMPLE 2C (3.683 g), 4-(((1R)-3-(dimethylamino)-1-((phenylsulfanyl)methyl)propyl)amino)-3-nitrobenzenesulfonamide (3.53 g), EDAC.HCl (3.32 g) and DMAP (2.12 g) in dichloromethane (500 mL) at 25° C. was stirred for 8 hours, washed with saturated NH4Cl (330 mL), and dried (MgSO4), filtered, and concentrated. The concentrate was flash chromatographed on silica gel with 1%, 2%, 5%, 10%, and 15% methanol/NH3-saturated dichloromethane. 1H NMR (DMSO-d6) δ 12.10 (br s, 1H), 11.18 (br s, 1H), 10.40 (br s, 1H), 8.54 (s, 1H), 8.29 (d, 1H), 8.10 (br s, 1H), 7.85 (d, 1H), 7.77 (d, 2H), 7.52 (d, 4H), 7.40-7.36 (m, 2H), 7.35-7.32 (m, 1H), 7.26-7.21 (m, 2H), 7.16-7.09 (m, 3H), 6.93 (d, 2H), 4.34 (br s, 2H), 4.35-4.23 (m, 1H), 3.88 (br s, 2H), 3.42-3.36 (m, 4H), 3.17-3.07 (m, 2H), 2.90-2.78 (m, 2H), 2.50 (s, 6H), 2.20-2.15 (m, 2H).

Workup

  1. washwashed with saturated NH4Cl (330 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on silica gel with 1%, 2%, 5%, 10%, and 15% methanol/NH3-saturated dichloromethane

Sources & evidence

ORD record
ord-aca2722671924307ba5d8ec1c1c1aa66
Source dataset
uspto-grants-2011_12
Patent number
US08084607B2

Reaction notes

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