Hydrochloride methanol → N-(4-Methylthio-5-isoquinolyl)-1,4-cyclohexanediamine hydrochloride

HRID 10535Notes

Reaction equation

HRID 10535 reaction equation
C(OC([NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([NH:15][C:16]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:17]=2[C:18]([S:26][CH3:27])=[CH:19][N:20]=[CH:21]3)[CH2:11][CH2:10]1)=O)(C)(C)C.[ClH:28].CO>>[ClH:28].[CH3:27][S:26][C:18]1[C:17]2[C:22](=[CH:23][CH:24]=[CH:25][C:16]=2[NH:15][CH:12]2[CH2:13][CH2:14][CH:9]([NH2:8])[CH2:10][CH2:11]2)[CH:21]=[N:20][CH:19]=1

Participants

3

Reactant 2

HCID 21893726Hydrochloride methanolHCID 21979943N-(tert-butoxycarbonyl)-N'-(4-methylthio-5-isoquinolyl)-1,4-cyclohexanediamine

Product 1

HCID 21979853N-(4-Methylthio-5-isoquinolyl)-1,4-cyclohexanediamine hydrochloride

Procedure

According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 78 (341 mg) and 10% hydrogen chloride/methanol solution (5 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with methanol (2 ml) and diethyl ether (6 ml). The deposited precipitates were collected by filtration and washed with diethyl ether to obtain the title compound (279 mg).

Workup

  1. custom(50° C., 2 hours)
  2. customthe solvent was evaporated under reduced pressure
  3. additionThe residue was added with methanol (2 ml) and diethyl ether (6 ml)
  4. customThe deposited precipitates
  5. filtrationwere collected by filtration
  6. washwashed with diethyl ether

Sources & evidence

ORD record
ord-b59867340aaa44959c4661c4e65259c3
Source dataset
uspto-grants-2006_08
Patent number
US07094789B2

Reaction notes

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