[(S)-1-(6-Fluoro-2,3,4,5-tetrahydro-1H-benzo[b]azepin-9-ylcarbamoyl)ethyl]carbamic acid tert-butyl ester → [(S)-1-(5-fluoro-6,7,8,9-tetrahydro-2,9a-diazabenzo[cd]azulen-1-yl)ethyl]carbamic acid tert-butyl ester

HRID 243209Notes

Reaction equation

HRID 243209 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][C@H:8]([C:10](=O)[NH:11][C:12]1[C:17]2[NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C:16]=2[C:15]([F:23])=[CH:14][CH:13]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]>CC(O)=O>[C:1]([O:5][C:6](=[O:25])[NH:7][C@H:8]([C:10]1[N:18]2[CH2:19][CH2:20][C:21]3[CH2:22][CH2:16][C:15]([F:23])=[CH:14][C:13]([C:17]=32)=[CH:12][N:11]=1)[CH3:9])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 1

HCID 68158139[(S)-1-(6-Fluoro-2,3,4,5-tetrahydro-1H-benzo[b]azepin-9-ylcarbamoyl)ethyl]carbamic acid tert-butyl ester

Product 1

HCID 68157976[(S)-1-(5-fluoro-6,7,8,9-tetrahydro-2,9a-diazabenzo[cd]azulen-1-yl)ethyl]carbamic acid tert-butyl esterYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of [(S)-1-(6-fluoro-2,3,4,5-tetrahydro-1H-benzo[b]azepin-9-ylcarbamoyl)ethyl]carbamic acid tert-butyl ester (270 mg, 0.768 mmol) in AcOH (4 mL) was stirred at 80° C. for 1 h, then concentrated in vacuo. The residue was purified by column chromatography (Si—PCC, gradient 30-60% EtOAc in cyclohexane) affording the title compound as a pale pink gum (252.6 mg, 99%). LCMS (Method B): RT 2.63 min [M+H]+ 334

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography (Si—PCC, gradient 30-60% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-38820dd36a4b423a85952ac649f6bb8e
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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