Hydrochloride methanol → N~1~-(4-Bromoisoquinolin-5-yl)cyclohexane-1,4-diamine--hydrogen chloride (1/1)

HRID 10533Notes

Reaction equation

HRID 10533 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]([Br:26])=[CH:19][N:20]=[CH:21]3)[CH2:11][CH2:10]1)=O)(C)(C)C.[ClH:27].CO>>[ClH:27].[Br: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 21979826N-(tert-butoxycarbonyl)-N'-(4-bromo-5-isoquinolyl)-1,4-cyclohexanediamine

Product 1

HCID 21979773N~1~-(4-Bromoisoquinolin-5-yl)cyclohexane-1,4-diamine--hydrogen chloride (1/1)

Procedure

According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 76 (124 mg) and 10% hydrogen chloride/methanol solution (3 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 (107 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-50d3985a248b4699b78cd3135ee56178
Source dataset
uspto-grants-2006_08
Patent number
US07094789B2

Reaction notes

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