Acetic Acid → HCID 68698620, compound

HRID 1444623Notes

Reaction equation

HRID 1444623 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11](C(O)=O)=[CH:12][C:13]=3[N:14]3[CH2:20][CH:19]([NH:21][CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])[CH2:18][C:17]4[CH:27]=[CH:28][CH:29]=[CH:30][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[C:35]([OH:37])=O.[CH2:38]=[O:39].[BH3-][C:41]#N.[Na+]>C(Cl)Cl.CCOC(C)=O>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:38]([O:37][CH3:35])=[O:39])=[CH:12][C:13]=3[N:14]3[CH2:20][CH:19]([N:21]([CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])[CH3:41])[CH2:18][C:17]4[CH:27]=[CH:28][CH:29]=[CH:30][C:16]=4[C:15]=23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 1170496713-cyclohexyl-6-{[2-(dimethylamino)ethyl]amino}-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylic acid

Product 1

HCID 68698620HCID 68698620, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 13-cyclohexyl-6-{[2-(dimethylamino)ethyl]-amino}-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate (prepared as in Example 5, Step 4) was dissolved in DCM (0.07 M) and pH adjusted to 6 with AcOH; 37% aq HCHO and, after half an hour NaCNBH3 (3 eq), were added and the mixture was stirred at RT overnight. The reaction mixture was diluted with EtOAc and washed with 1N NaOH and brine, dried and evaporated affording methyl 13-cyclohexyl-6-{[2-(dimethylamino)ethyl][(methyl) amino]}-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate. Hydrolysis of the foregoing methyl ester was done with 1M aqueous KOH (6 eq) in dioxane (0.IM) at 60 ° C.; the reaction was complete in 2 h, and the title compound was obtained in 20% yield after RP-HPLC purification and lyophilisation (Conditions: Column: Waters X-TERRA MS C18, 10 micron, 19×150 mm; Gradient: A: H2O+0.1% TFA; B: MeCN+0.1% TFA; 75% A isocratic for 3 min, linear to 20% A in 12 min).

Workup

  1. additionwere added
  2. washwashed with 1N NaOH and brine
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-504ad893b1f44458aae91d50b280e434
Source dataset
uspto-grants-2010_02
Patent number
US07662809B2

Reaction notes

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