Dichloromethane → HCID 68620864, compound

HRID 1244693Notes

Reaction equation

HRID 1244693 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[C:6]([O:10][C:11](=[O:36])[NH:12][CH:13]1[CH:30]([NH:31][CH2:32][CH2:33][CH:34]=[CH2:35])[CH2:29][N:16]2[CH2:17][CH2:18][C:19]3[C:24]([CH:15]2[CH2:14]1)=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=3)([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C.[Cl:44][CH2:45][Cl:46]>>[CH2:45]([Cl:46])[Cl:44].[CH3:1][OH:4].[NH4+:12].[OH-:10].[C:6]([O:10][C:11](=[O:36])[NH:12][CH:13]1[CH:30]([N:31]([C:1](=[O:4])[CH:2]=[CH2:3])[CH2:32][CH2:33][CH:34]=[CH2:35])[CH2:29][N:16]2[CH2:17][CH2:18][C:19]3[C:24]([CH:15]2[CH2:14]1)=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=3)([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 68620413HCID 68620413, compound

Product 2

HCID 21896990Dichloromethane methanol ammonium hydroxideHCID 68620864HCID 68620864, compoundYield 75%

Procedure

Acryloyl chloride (18 mg, 0.20 mmol) was added dropwise at 0° C. to a solution of (RS,RS,RS)-(3-but-3-enylamino-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-yl)-carbamic acid tert-butyl ester (77 mg, 0.18 mmol) and triethylamine (20 mg, 0.20 mmol) in dichloromethane (1.5 mL). After 30 min at 0° C. the reaction mixture was partitioned between 2 M aq. sodium carbonate solution and ethyl acetate. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, CH2Cl2/MeOH/NH4OH 95:5:0.25) afforded the title compound (65 mg, 75%). White solid, MS (ISP) 486.5 (M+H)+.

Workup

  1. customAfter 30 min at 0° C. the reaction mixture was partitioned between 2 M aq. sodium carbonate solution and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-a2c982e1f27a497f9889d0337847cae5
Source dataset
uspto-grants-2006_10
Patent number
US07122555B2

Reaction notes

Loading…