HCID 70896225, compound → HCID 70896224, compound

HRID 2369884Notes

Reaction equation

HRID 2369884 reaction equation
[Cl:1][C:2]1[C:13]2[C:14]3[N:6]([NH:7][CH2:8][C:9]=3[C@H:10]([CH:16]3[CH:21]4[CH2:22][CH2:23][N:18]([CH2:19][CH2:20]4)[CH2:17]3)[C:11](=[O:15])[CH:12]=2)[CH:5]=[CH:4][N:3]=1>Cl.CO>[ClH:1].[Cl:1][C:2]1[C:13]2[C:14]3[N:6]([NH:7][CH2:8][C:9]=3[C@H:10]([CH:16]3[CH:21]4[CH2:22][CH2:23][N:18]([CH2:19][CH2:20]4)[CH2:17]3)[C:11](=[O:15])[CH:12]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 70896225HCID 70896225, compound

Product 1

HCID 70896224HCID 70896224, compoundYield 150.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

(S)-4-chloro-7-(quinuclidin-3-yl)-8,9-dihydro-[1,4]diazepino[6,7,1-hi]indazol-6(7H)-one (428 mg, 1.30 mmol) from Step F above was dissolved in 1.25 M HCl in CH3OH and concentrated under reduced pressure. The resulting yellow-green solid was triturated (MeOH/DCM/diethyl ether), filtered and dried under high vacuum to give (S)-4-chloro-7-(quinuclidin-3-yl)-8,9-dihydro-[1,4]diazepino[6,7,1-hi]indazol-6(7H)-one hydrochloride as a yellow solid (359 mg, 31%): 1H NMR (500 MHz, D2O) δ 7.81 (s, 1H), 7.68 (s, 2H), 4.43-4.20 (m, 3H), 3.80-3.65 (m, 1H), 3.65-3.50 (m, 1H), 3.40-3.20 (m, 2H), 3.20-3.00 (m, 4H), 2.26 (s, 1H), 2.00-1.70 (m, 4H); MS (ESI+) m/z 331 (M+H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe resulting yellow-green solid was triturated (MeOH/DCM/diethyl ether)
  3. filtrationfiltered
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-97af508161de435b9d7f5609b0e14123
Source dataset
uspto-grants-2014_04
Patent number
US08710046B2

Reaction notes

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