Hydrochloric Acid → 2-[(6S,9R)-9-amino-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl]propan-2-ol

HRID 1664948Notes

Reaction equation

HRID 1664948 reaction equation
Cl.[F:2][C:3]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][C:4]=1[C@H:10]1[CH2:16][N:15]2[C:17]([C:20]([OH:23])([CH3:22])[CH3:21])=[N:18][N:19]=[C:14]2[C@H:13]([NH:24]C(=O)OC(C)(C)C)[CH2:12][CH2:11]1>O1CCOCC1>[NH2:24][C@@H:13]1[CH2:12][CH2:11][C@@H:10]([C:4]2[CH:5]=[CH:6][CH:7]=[C:8]([F:9])[C:3]=2[F:2])[CH2:16][N:15]2[C:17]([C:20]([OH:23])([CH3:21])[CH3:22])=[N:18][N:19]=[C:14]12

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86620147tert-butyl [(6S,9R)-6-(2,3-difluorophenyl)-3-(1-hydroxy-1-methylethyl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-9-yl]carbamate

Product 1

HCID 674393392-[(6S,9R)-9-amino-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl]propan-2-olYield 130.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Hydrochloric acid (4.0 M in dioxane; 5 mL, 20.0 mmol) was added to a solution of tert-butyl [(6S,9R)-6-(2,3-difluorophenyl)-3-(1-hydroxy-1-methylethyl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-9-yl]carbamate (176 mg, 0.417 mmol) in 1,4-dioxane (5 mL). After 1 h, the reaction mixture was concentrated to give the bis hydrochloride salt of the title compound (175 mg). MS 323.1 (M+1).

Workup

  1. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-c676069a44e049918d942fb1ee9c32dc
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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