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Hydrochloric Acid → N-[4-(5,6,7,8-Tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl)phenyl]methanesulfonamide

HRID 1364131
Notes
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Reaction equation

HRID 1364131 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:21]=[C:20]3[C:14]([CH2:15][CH2:16][N:17](C(OC(C)(C)C)=O)[CH2:18][CH2:19]3)=[N:13]2)=[CH:8][CH:7]=1)(=[O:4])=[O:3].Cl>O1CCOCC1.CO>[N:13]1[N:12]([C:9]2[CH:8]=[CH:7][C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:11][CH:10]=2)[CH:21]=[C:20]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15][C:14]=12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 669308081,1-Dimethylethyl 2-{4-[(methylsulfonyl)amino]phenyl}-4,5,7,8-tetrahydropyrazolo[3,4-d]azepine-6(2H)-carboxylate

Product 1

HCID 66930788N-[4-(5,6,7,8-Tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl)phenyl]methanesulfonamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-Dioxane
Solvent
2×

Procedure

To a solution of 1,1-dimethylethyl 2-{4-[(methylsulfonyl)amino]phenyl}-4,5,7,8-tetrahydropyrazolo[3,4-d]azepine-6(2H)-carboxylate (may be prepared as described in Description 39) (16 mg, 0.039 mmol) in dioxan (1 ml) was added 4M hydrochloric acid in dioxan (2 ml). The resulting mixture was stirred at room temperature, under argon, overnight. The reaction mixture was diluted with methanol and then purified by SCX, eluting with methanol and then 2M ammonia/methanol. The basic fractions were combined and solvent evaporated in vacuo to afford the title compound (D40). MS (ES+) m/e 307 [M+H]+.

Workup

  1. custompurified by SCX
  2. washeluting with methanol
  3. customsolvent evaporated in vacuo

Sources & evidence

ORD record
ord-c42726a43a1b4ea6989e606bfb2eb298
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07888347B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes