Hydrochloric Acid → 6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indole-2(1H)-carboximidamide

HRID 1505728Notes

Reaction equation

HRID 1505728 reaction equation
C(OC(=O)[NH:7]/[C:8](=[N:34]\C(OC(C)(C)C)=O)/[CH:9]1[NH:21][CH2:20][C:18]2=[C:19]3[C:14](=[C:15]([C:30]([F:33])([F:32])[F:31])[C:16]([CH2:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:17]2)[CH:13]=[CH:12][N:11]3[CH2:10]1)(C)(C)C.Cl>C(Cl)Cl.O1CCOCC1>[CH2:22]([C:16]1[C:15]([C:30]([F:33])([F:32])[F:31])=[C:14]2[C:19]3=[C:18]([CH2:20][NH:21][CH:9]([C:8](=[NH:7])[NH2:34])[CH2:10][N:11]3[CH:12]=[CH:13]2)[CH:17]=1)[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 140613434tert-butyl (NZ)-N-[[(2-methylpropan-2-yl)oxycarbonylamino]-[6-(2-phenylethyl)-5-(trifluoromethyl)-1,10-diazatricyclo[6.4.1.04,13]trideca-2,4(13),5,7-tetraen-11-yl]methylidene]carbamate

Product 1

HCID 866919976-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indole-2(1H)-carboximidamideYield 51.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of Z-tert-butyl(((tert-butoxycarbonyl)imino)(6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indol-2(1H)-yl)methyl)carbamate (74 mg, 0.13 mmol) in CH2Cl2 (5 mL) was treated with 4M HCl in 1,4-dioxane (12 mL) and the resulting mixture was stirred at room temperature overnight. Evaporation of the solvent and trituration with diethyl ether yielded 6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indole-2(1H)-carboximidamide (26 mg).

Workup

  1. customEvaporation of the solvent and trituration with diethyl ether

Sources & evidence

ORD record
ord-69e69117d990487b966ef799d2cbf464
Source dataset
uspto-grants-2015_12
Patent number
US09216998B2

Reaction notes

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