Trifluoroacetic acid methylene chloride → (2r)-2-Amino-2-cyclohexyl-n-(6-oxo-2-phenyl-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)ethanamide trifluoroacetate

HRID 720110Notes

Reaction equation

HRID 720110 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.[C:39]([OH:45])([C:41]([F:44])([F:43])[F:42])=[O:40].C(Cl)Cl>CO.C(OCC)C>[F:42][C:41]([F:44])([F:43])[C:39]([OH:45])=[O:40].[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 21863450Trifluoroacetic acid methylene chlorideHCID 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 136401881(2r)-2-Amino-2-cyclohexyl-n-(6-oxo-2-phenyl-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)ethanamide trifluoroacetateYield 78%

Reagents, catalysts & solvents 1

HCID 21864698Diethyl ether methanolSolvent

Procedure

Preparation of example 60 from the title compound of Example 59 (90 mg, 0.17 mmol), and 1:1 TFA/CH2Cl2 (5 mL) was carried out analogously to Example 20. Isolation, also in an analogous manner, included a further trituration with methanol/diethyl ether and afforded the title compound (70 mg, 0.013 mmol) as an orange/yellow powder in 78% yield.

Sources & evidence

ORD record
ord-c7ed4714888f426a8fc98243152b74c4
Source dataset
uspto-grants-2006_11
Patent number
US07132533B2

Reaction notes

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