Hydrochloric Acid → (2r)-2-Amino-2-(4-hydroxyphenyl)-n-(6-oxo-2-phenyl-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)ethanamide hydrochloride

HRID 2375104Notes

Reaction equation

HRID 2375104 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:32]C(=O)OC(C)(C)C)[C:9](=[O:31])[NH:10][C:11]2[CH:12]=[C:13]3[C:29](=[O:30])[NH:28][N:27]=[CH:26][C:15]4=[C:16]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[NH:17][C:18]([CH:19]=2)=[C:14]34)=[CH:4][CH:3]=1.[ClH:40].C(N(CC)CC)C>O1CCOCC1>[ClH:40].[NH2:32][C@H:8]([C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)[C:9]([NH:10][C:11]1[CH:12]=[C:13]2[C:29](=[O:30])[NH:28][N:27]=[CH:26][C:15]3=[C:16]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[NH:17][C:18]([CH:19]=1)=[C:14]23)=[O:31]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 1361816521,1-Dimethylethyl (1R)-1-(4-hydroxyphenyl)-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 136401950(2r)-2-Amino-2-(4-hydroxyphenyl)-n-(6-oxo-2-phenyl-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)ethanamide hydrochlorideYield 60%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Preparation of example 175 from the title compound of Example 153 (38 mg, 0.072 mmol) and 4M HCl in dioxane (10 mL) was carried out analogously to Example 91. Isolation, also in an analogous manner, included freebasing with triethylamine and subsequent silica gel chromatography eluting with 3:1:1 hexane:ethyl acetate:ethanol. With ice bath cooling, the purified freebase in CH2Cl2 (10 mL) was treated with 4M HCl in dioxane (0.1 mL). After removal of the volatile components, the title compound (20 mg, 0.043 mmol) was obtained as an orange/yellow powder in 60% yield.

Workup

  1. washeluting with 3:1:1 hexane
  2. temperatureWith ice bath cooling
  3. additionthe purified freebase in CH2Cl2 (10 mL) was treated with 4M HCl in dioxane (0.1 mL)
  4. customAfter removal of the volatile components

Sources & evidence

ORD record
ord-a738eb06a5504094b65d6fdc1590d2f1
Source dataset
uspto-grants-2008_12
Patent number
US07462713B2

Reaction notes

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