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Diethyl Ether → (7R)-7-Amino-4-chloro-9-(2,2,2-trifluoroethyl)-6,7,9,10-tetrahydroazepino[3,4-e]indazol-8(3H)-one bis-methanesulfonate

HRID 552568
Notes
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Reaction equation

HRID 552568 reaction equation
C(OC(=O)[NH:10][C@H:11]1[C:25](=[O:26])[N:24]([CH2:27][C:28]([F:31])([F:30])[F:29])[CH2:23][C:14]2[C:15]3[CH:16]=[N:17][NH:18][C:19]=3[C:20]([Cl:22])=[CH:21][C:13]=2[CH2:12]1)C1C=CC=CC=1.C1(OC)C=CC=CC=1.[CH3:41][S:42]([OH:45])(=[O:44])=[O:43].CCOCC>C(Cl)Cl>[CH3:41][S:42]([OH:45])(=[O:44])=[O:43].[CH3:41][S:42]([OH:45])(=[O:44])=[O:43].[NH2:10][C@H:11]1[C:25](=[O:26])[N:24]([CH2:27][C:28]([F:29])([F:31])[F:30])[CH2:23][C:14]2[C:15]3[CH:16]=[N:17][NH:18][C:19]=3[C:20]([Cl:22])=[CH:21][C:13]=2[CH2:12]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6395Methanesulfonic AcidHCID 7519AnisoleHCID 59732091(R)-Benzyl 4-chloro-8-oxo-9-(2,2,2-trifluoroethyl)-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-ylcarbamate

Product 1

HCID 86640003(7R)-7-Amino-4-chloro-9-(2,2,2-trifluoroethyl)-6,7,9,10-tetrahydroazepino[3,4-e]indazol-8(3H)-one bis-methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of benzyl[(7R)-4-chloro-8-oxo-9-(2,2,2-trifluoroethyl)-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-yl]carbamate from Step A (265 mg, 0.568 mmol) and anisole (184 mg, 1.70 mmol) in CH2Cl2 (4 mL) was added methanesulfonic acid (1.84 mL, 28 mmol). The resulting mixture was stirred at ambient temperature for 45 min, Et2O (45 mL) was added, and stirring was continued for 20 min. The supernatant was removed and the residue was washed with Et2O and dried in vacuo to give the title compound. MS: m/z=333.

Workup

  1. stirringstirring
  2. waitwas continued for 20 min
  3. customThe supernatant was removed
  4. washthe residue was washed with Et2O
  5. customdried in vacuo

Sources & evidence

ORD record
ord-ab5af4adb1ac466bbc1ec3bb9fbe800b
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07951795B2

Reaction notes

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