1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → tert-butyl {2-[{[6-({benzyl[(3-chloropropyl)sulfonyl]amino}carbonyl)-3-cyclohexyl-2-phenyl-1H-indol-1-yl]acetyl}(methyl)amino]ethyl}methylcarbamate

HRID 505397Notes

Reaction equation

HRID 505397 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:40])[CH2:9][CH2:10][N:11]([CH3:39])[C:12](=[O:38])[CH2:13][N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:23](O)=[O:24])[CH:21]=2)[C:16]([CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[C:15]1[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:41]([NH:48][S:49]([CH2:52][CH2:53][CH2:54][Cl:55])(=[O:51])=[O:50])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:41]([N:48]([S:49]([CH2:52][CH2:53][CH2:54][Cl:55])(=[O:51])=[O:50])[C:23]([C:20]1[CH:21]=[C:22]2[C:17]([C:16]([CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)=[C:15]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[N:14]2[CH2:13][C:12]([N:11]([CH3:39])[CH2:10][CH2:9][N:8]([CH3:40])[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:38])=[CH:18][CH:19]=1)=[O:24])[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 43654054HCID 43654054, compound2×HCID 66674585HCID 66674585, compound

Product 1

HCID 66674974tert-butyl {2-[{[6-({benzyl[(3-chloropropyl)sulfonyl]amino}carbonyl)-3-cyclohexyl-2-phenyl-1H-indol-1-yl]acetyl}(methyl)amino]ethyl}methylcarbamate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

A solution of the crude 1-{2-[{2-[(tert-butoxycarbonyl)(methyl)amino]ethyl}(methyl)amino]-2-oxoethyl}-3-cyclohexyl-2-phenyl-1H-indole-6-carboxylic acid in DCM (0.04 M) was treated with DMAP (2.5 eq), N-benzyl-3-chloropropane-1-sulfonamide (1.5 eq) and EDAC.HCl (1.5 eq). The reaction was left stirring at 40° C. overnight. Further DMAP (2.5 eq), N-benzyl-3-chloropropane-1-sulfonamide (1.5 eq) and EDAC.HCl (1.5 eq) were added and the reaction left to stir at 40° C. for another night. The mixture was diluted with DCM and washed with an aqueous solution of HCl (1N), a saturated aqueous solution of NaHCO3 and brine before being dried over Na2SO4, filtered and concentrated in vacuo. The crude was then used in the next step without any further purification. (ES+) m/z 777 (M+H)+

Workup

  1. waitThe reaction was left
  2. waitthe reaction left
  3. stirringto stir at 40° C. for another night
  4. washwashed with an aqueous solution of HCl (1N)
  5. dry with materiala saturated aqueous solution of NaHCO3 and brine before being dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude was then used in the next step without any further purification

Sources & evidence

ORD record
ord-840d17a3ceef4432b9eb18c1130840bc
Source dataset
uspto-grants-2010_08
Patent number
US07781422B2

Reaction notes

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