1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 46831860, compound

HRID 2273731Notes

Reaction equation

HRID 2273731 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([O:10][C:11]3[CH:19]=[C:18]([N:20]4[CH2:25][CH2:24][N:23]([CH:26]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=5[C:34]5[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=5)[CH3:27])[CH2:22][CH2:21]4)[CH:17]=[CH:16][C:12]=3[C:13](O)=[O:14])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[N+:41]([C:44]1[CH:45]=[C:46]([S:58]([NH2:61])(=[O:60])=[O:59])[CH:47]=[CH:48][C:49]=1[NH:50][CH2:51][CH:52]1[CH2:57][CH2:56][O:55][CH2:54][CH2:53]1)([O-:43])=[O:42].Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.ClCCl>[Cl:40][C:37]1[CH:36]=[CH:35][C:34]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[CH:26]([N:23]2[CH2:22][CH2:21][N:20]([C:18]3[CH:17]=[CH:16][C:12]([C:13]([NH:61][S:58]([C:46]4[CH:47]=[CH:48][C:49]([NH:50][CH2:51][CH:52]5[CH2:53][CH2:54][O:55][CH2:56][CH2:57]5)=[C:44]([N+:41]([O-:43])=[O:42])[CH:45]=4)(=[O:59])=[O:60])=[O:14])=[C:11]([O:10][C:5]4[CH:6]=[CH:7][CH:8]=[C:9]5[C:4]=4[CH:3]=[CH:2][NH:1]5)[CH:19]=3)[CH2:25][CH2:24]2)[CH3:27])=[CH:39][CH:38]=1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 574749533-nitro-4-((tetrahydro-2H-pyran-4-yl)MethylaMino)benzenesulfonaMideHCID 67227358HCID 67227358, compound

Product 1

HCID 46831860HCID 46831860, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of EXAMPLE 175E (66 mg), 3-nitro-4-((tetrahydro-2H-pyran-4-yl)methylamino)benzenesulfonamide (75 mg) and 4-dimethylaminopyridine (58.4 mg) in dichloromethane (5 mL) was added 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (45.8 mg). The mixture was stirred at ambient temperature overnight and concentrated. The concentrate was purified by RP HPLC (10-70% acetonitrile in 0.1% trifluoroacetic acid water/70 minutes). The desired fractions were concentrated to remove acetonitrile and the concentrate was diluted with dichloromethane and neutralized with aqueous NaHCO3. The dichloromethane layer was dried over Na2SO4 and concentrated to provide the title compound. 1H NMR (500 MHz, dimethysulfoxide-d6) δ ppm 11.31 (1H, s), 11.25 (1H, s), 8.62 (1H, t), 8.50 (1H, d), 7.68 (1H, dd), 7.53 (2H, d), 7.46 (2H, d), 7.37 (1H, t), 7.24-7.31 (4H, m), 7.17 (1H, d), 7.12 (1H, dd), 7.07 (1H, d), 6.96 (1H, t), 6.69 (1H, dd), 6.42 (1H, d), 6.26 (2H, s), 3.85 (2H, dd), 3.21-3.33 (5H, m), 3.01 (4H, s), 2.29-2.39 (2H, m), 2.15-2.22 (2H, m), 1.83-1.94 (1H, m), 1.57-1.68 (2H, m), 1.22-1.31 (2H, m), 1.17 (3H, d).

Workup

  1. concentrationconcentrated
  2. customThe concentrate was purified by RP HPLC (10-70% acetonitrile in 0.1% trifluoroacetic acid water/70 minutes)
  3. concentrationThe desired fractions were concentrated
  4. customto remove acetonitrile
  5. additionthe concentrate was diluted with dichloromethane and neutralized with aqueous NaHCO3
  6. dry with materialThe dichloromethane layer was dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c55b7ce0c5a14e049c0ebe0c2096f475
Source dataset
uspto-grants-2015_09
Patent number
US09125913B2

Reaction notes

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