Dichloromethane → HCID 68698526, compound

HRID 1444631Notes

Reaction equation

HRID 1444631 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:32]([O:34]C)=[O:33])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[N:18]([CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])[C:17](=[O:31])[CH2:16][CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)Cl>>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:32]([OH:34])=[O:33])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[N:18]([CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])[C:17](=[O:31])[CH2:16][CH2:15]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 68699389Methyl 14-cyclohexyl-5-[2-(dimethylamino)ethyl]-6-oxo-5,6,7,8-tetrahydroindolo[1,2-e][1,5]benzodiazocine-11-carboxylate

Product 1

HCID 68698526HCID 68698526, compoundYield 40%

Procedure

To a solution of methyl 14-cyclohexyl-5-[2-(dimethylamino)ethyl]-6-oxo-5,6,7,8-tetrahydroindolo[1,2-e][1,5]benzodiazocine-11-carboxylate in DCM (0.1M) 7 eq BBr3 (1M solution in DCM) were added. The solution stirred at RT for 20 mins. The volatiles were evaporated in vacuo. The crude was then purified by prep RP-HPLC (stationary phase: column Waters XTERRA prep. C18, 5 um, 19×150 mm. Mobile phase: MeCN/H2O buffered with 0.1% TFA). Fractions containing the pure compound were combined and freeze dried to afford the title compound (40% over two steps).

Workup

  1. customThe volatiles were evaporated in vacuo
  2. customThe crude was then purified by prep RP-HPLC (stationary phase: column Waters XTERRA prep. C18, 5 um, 19×150 mm. Mobile phase: MeCN/H2O buffered with 0.1% TFA)
  3. additionFractions containing the pure compound
  4. customfreeze dried

Sources & evidence

ORD record
ord-1c272126ac26426b9743258a708fd9c0
Source dataset
uspto-grants-2010_02
Patent number
US07662809B2

Reaction notes

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