Diisopropylethylamine → methyl 15-cyclohexyl-6-[2-(dimethylamino)ethyl]-7-oxo-6,7,8,9-tetrahydro-5H-indolo[2,1-a][2,6]benzodiazonine-12-carboxylate

HRID 1714074Notes

Reaction equation

HRID 1714074 reaction equation
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:20][CH2:21][C:22]([OH:24])=O)[C:8]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH2:31][NH:32][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl.CCOC(C)=O.Cl>[CH:1]1([C:7]2[C:15]3[CH:14]=[CH:13][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:11][C:10]=3[N:9]3[CH2:20][CH2:21][C:22](=[O:24])[N:32]([CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])[CH2:31][C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=4[C:8]=23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 685099363-[3-cyclohexyl-2-[2-({[2-(dimethylamino)ethyl]amino}methyl)phenyl]-6-(methoxycarbonyl)-1H-indol-1-yl]propanoic acid

Product 1

HCID 68502286methyl 15-cyclohexyl-6-[2-(dimethylamino)ethyl]-7-oxo-6,7,8,9-tetrahydro-5H-indolo[2,1-a][2,6]benzodiazonine-12-carboxylate

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-[3-cyclohexyl-2-[2-({[2-(dimethylamino)ethyl]amino}methyl)phenyl]-6-(methoxycarbonyl)-1H-indol-1-yl]propanoic acid in DCM (0.01 M), 3.5 eq of DIPEA and 1.5 eq of HATU were added and the mixture was stirred at RT for 4 h. The solution was diluted with EtOAc and HCl (1 N), the aqueous phase was re-extracted with EtOAc (twice) and the combined organics then washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude was used in the next step without further purification; MS (ES+) m/z 488 (M+H)+.

Workup

  1. extractionthe aqueous phase was re-extracted with EtOAc (twice) and the combined organics
  2. washthen washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude was used in the next step without further purification

Sources & evidence

ORD record
ord-a55af7a9838040cabb766ca8730d6d54
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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