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

HRID 1364115Notes

Reaction equation

HRID 1364115 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:18]=[C:17]3[C:11]([CH2:12][CH2:13][N:14](C(OC(C)(C)C)=O)[CH2:15][CH2:16]3)=[N:10]2)=[CH:5][CH:4]=1)#[N:2].Cl.CO>O1CCOCC1>[N:10]1[N:9]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH:18]=[C:17]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12][C:11]=12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 669307651,1-Dimethylethyl 2-(4-cyanophenyl)-4,5,7,8-tetrahydropyrazolo[3,4-d]azepine-6(2H)-carboxylate

Product 1

HCID 669308824-(5,6,7,8-Tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

1,1-Dimethylethyl 2-(4-cyanophenyl)-4,5,7,8-tetrahydropyrazolo[3,4-d]azepine-6(2H)-carboxylate (may be prepared as described in Description 10) (150 mg, 0.443 mmol) was dissolved in 1,4-dioxan (ml) and 4M hydrogen chloride in 1,4-dioxan (3 ml) added. The mixture was stirred at room temperature for 2 hours. Methanol was added and the mixture purified on 10 g SCX column, eluting initially with methanol, than with 2M ammonia in methanol. Evaporation of the basic fractions gave the title compound (D11). MS (ES+) m/e 239 [M+H]+

Workup

  1. customthe mixture purified on 10 g SCX column
  2. washeluting initially with methanol, than with 2M ammonia in methanol
  3. customEvaporation of the basic fractions

Sources & evidence

ORD record
ord-faac9d9f5cc74d6b81fcbc29105ca845
Source dataset
uspto-grants-2011_02
Patent number
US07888347B2

Reaction notes

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