Hydrochloric Acid → (2R)-2-Amino-2-cyclohexyl-N-(6-oxo-2-phenyl-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indol-8-yl)-acetamide

HRID 2375081Notes

Reaction equation

HRID 2375081 reaction equation
[CH:1]1([C@@H:7]([NH:31]C(=O)OC(C)(C)C)[C:8](=[O:30])[NH:9][C:10]2[CH:11]=[C:12]3[C:28](=[O:29])[NH:27][N:26]=[CH:25][C:14]4=[C:15]([C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=5)[NH:16][C:17]([CH:18]=2)=[C:13]34)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>O1CCOCC1>[NH2:31][C@H:7]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C:8]([NH:9][C:10]1[CH:11]=[C:12]2[C:28](=[O:29])[NH:27][N:26]=[CH:25][C:14]3=[C:15]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[NH:16][C:17]([CH:18]=1)=[C:13]23)=[O:30]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 136181616tert-Butyl (1R)-1-cyclohexyl-2-oxo-2-[(6-oxo-2-phenyl-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indol-8-yl)amino]ethylcarbamate

Product 1

HCID 136141701(2R)-2-Amino-2-cyclohexyl-N-(6-oxo-2-phenyl-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indol-8-yl)-acetamideYield 87.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The title compound of Example 59 (210 mg, 0.41 mmol) was treated with 4M HCl in dioxane and allowed to stir tightly capped as a slurry for about 4 hours after which the volatile components were evaporated and diethyl ether was added and evaporated several times. The resulting solids were dissolved in methanol, precipitated with diethyl ether, and collected to afford the title compound (161 mg, 0.36 mmol) as a yellow powder in 87% yield.

Workup

  1. customcapped as a slurry for about 4 hours after which the volatile components
  2. customwere evaporated
  3. additiondiethyl ether was added
  4. customevaporated several times
  5. dissolutionThe resulting solids were dissolved in methanol
  6. customprecipitated with diethyl ether
  7. customcollected

Sources & evidence

ORD record
ord-aed5ea7365314e7f8422c5a7404c99fe
Source dataset
uspto-grants-2008_12
Patent number
US07462713B2

Reaction notes

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