Hydrochloride methanol → N-(5-Isoquinolyl)-1,3-xylylenediamine hydrochloride

HRID 10524Notes

Reaction equation

HRID 10524 reaction equation
C(OC([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][NH:17][C:18]2[CH:27]=[CH:26][CH:25]=[C:24]3[C:19]=2[CH:20]=[CH:21][N:22]=[CH:23]3)[CH:11]=1)=O)(C)(C)C.[ClH:28].CO>>[ClH:28].[CH:23]1[C:24]2[C:19](=[C:18]([NH:17][CH2:16][C:12]3[CH:13]=[CH:14][CH:15]=[C:10]([CH2:9][NH2:8])[CH:11]=3)[CH:27]=[CH:26][CH:25]=2)[CH:20]=[CH:21][N:22]=1

Participants

3

Reactant 2

HCID 21893726Hydrochloride methanolHCID 69524501N-(tert-butoxycarbonyl)-N'-(5-isoquinolyl)-1,3-xylylenediamine

Product 1

HCID 69524206N-(5-Isoquinolyl)-1,3-xylylenediamine hydrochloride

Procedure

According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 44 (364 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 (1 ml) and diethyl ether (3 ml). The deposited precipitates were collected by filtration and washed with diethyl ether to obtain the title compound (316 mg) as light yellow powdery solid.

Workup

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

Sources & evidence

ORD record
ord-c1897e61e42c4a49b6fe74b11d882df6
Source dataset
uspto-grants-2006_08
Patent number
US07094789B2

Reaction notes

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