Hydrochloric Acid → (2r)-2-Amino-3-(4-fluorophenyl)-n-(6-oxo-2-phenyl-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)propanamide hydrochloride

HRID 720140Notes

Reaction equation

HRID 720140 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:33]C(=O)OC(C)(C)C)[C:10](=[O:32])[NH:11][C:12]2[CH:13]=[C:14]3[C:30](=[O:31])[NH:29][N:28]=[CH:27][C:16]4=[C:17]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)[NH:18][C:19]([CH:20]=2)=[C:15]34)=[CH:4][CH:3]=1.[ClH:41].C(N(CC)CC)C>O1CCOCC1>[ClH:41].[NH2:33][C@H:9]([CH2:8][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[C:10]([NH:11][C:12]1[CH:13]=[C:14]2[C:30](=[O:31])[NH:29][N:28]=[CH:27][C:16]3=[C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[NH:18][C:19]([CH:20]=1)=[C:15]23)=[O:32]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 1361816201,1-Dimethylethyl (1R)-1-[(4-fluorophenyl)methyl]-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 136401933(2r)-2-Amino-3-(4-fluorophenyl)-n-(6-oxo-2-phenyl-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)propanamide hydrochlorideYield 49%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Preparation of example 168 from the title compound of Example 152 (49 mg, 0.091 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 (21 mg, 0.044 mmol) was obtained as an orange/yellow powder in 49% 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-7787566e29fe4a09bc8e61716e9f3b7c
Source dataset
uspto-grants-2006_11
Patent number
US07132533B2

Reaction notes

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