Diisopropylcarbodiimide → methyl(7R)-7-[{2-[[4-(aminosulfonyl)butanoyl](methyl)amino]ethyl}(methyl)-amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

HRID 421946Notes

Reaction equation

HRID 421946 reaction equation
[NH2:1][S:2]([CH2:5][CH2:6][CH2:7][C:8]([OH:10])=O)(=[O:4])=[O:3].CCN(C(C)C)C(C)C.CC(C)N=C=NC(C)C.C1C=CC2N(O)N=NC=2C=1.[CH:39]1([C:45]2[C:46]3[CH:47]=[CH:48][C:49]([C:70]([O:72][CH3:73])=[O:71])=[CH:50][C:51]=3[N:52]3[C:59]=2[C:58]2[CH:60]=[CH:61][CH:62]=[CH:63][C:57]=2[O:56][CH2:55][C@H:54]([N:64]([CH3:69])[CH2:65][CH2:66][NH:67][CH3:68])[CH2:53]3)[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1>CN(C=O)C>[NH2:1][S:2]([CH2:5][CH2:6][CH2:7][C:8]([N:67]([CH3:68])[CH2:66][CH2:65][N:64]([CH3:69])[C@@H:54]1[CH2:53][N:52]2[C:51]3[CH:50]=[C:49]([C:70]([O:72][CH3:73])=[O:71])[CH:48]=[CH:47][C:46]=3[C:45]([CH:39]3[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]3)=[C:59]2[C:58]2[CH:60]=[CH:61][CH:62]=[CH:63][C:57]=2[O:56][CH2:55]1)=[O:10])(=[O:4])=[O:3]

Participants

7

Reactant 5

HCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27733204-sulfamoylbutanoic AcidHCID 66675300methyl(7R)-14-cyclohexyl-7-{methyl[2-(methylamino)ethyl]amino}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Product 1

HCID 66674679methyl(7R)-7-[{2-[[4-(aminosulfonyl)butanoyl](methyl)amino]ethyl}(methyl)-amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(aminosulfonyl)butanoic acid (1.2 eq.), DIPEA (2 eq.), DIC (1.1 eq.) and HOBT (1.1 eq.) were added to a solution of methyl(7R)-14-cyclohexyl-7-{methyl[2-(methylamino)ethyl]amino}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (0.07 M) in DMF. The reaction was stirred under N2 at RT overnight. The mixture was then partitioned between sat. aq. NaHCO3 and EtOAc. The combined organics were washed with 1N HCl followed by brine, dried (Na2SO4), filtered and concentrated in vacuo. The product was used in the next step without further purification. (ES+) m/z 625 (M+H)+.

Workup

  1. customThe mixture was then partitioned between sat. aq. NaHCO3 and EtOAc
  2. washThe combined organics were washed with 1N HCl
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe product was used in the next step without further purification

Sources & evidence

ORD record
ord-8c935babb3b642998f6c250fafe34aa2
Source dataset
uspto-grants-2012_01
Patent number
US08101595B2

Reaction notes

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