Triethylamine → N-(tert-butoxycarbonyl)-N'-[(1-chloro-5-isoquinolyl)sulfonyl]-1,3-propylenediamine

HRID 10498

Reaction equation

HRID 10498 reaction equation
[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][CH2:9][CH2:10][NH2:11])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl:20][C:21]1[C:30]2[C:25](=[C:26]([S:31](Cl)(=[O:33])=[O:32])[CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][N:22]=1.Cl.ClC1C2C(=C(S(Cl)(=O)=O)C=CC=2)C=CN=1>ClCCl>[C:1]([O:5][C:6]([NH:7][CH2:8][CH2:9][CH2:10][NH:11][S:31]([C:26]1[CH:27]=[CH:28][CH:29]=[C:30]2[C:25]=1[CH:24]=[CH:23][N:22]=[C:21]2[Cl:20])(=[O:33])=[O:32])=[O:12])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 219797811-Chloroisoquinoline-5-sulfonyl chlorideHCID 219799361-Chloroisoquinoline-5-sulfonyl chloride hydrochloride

Product 1

HCID 21979832N-(tert-butoxycarbonyl)-N'-[(1-chloro-5-isoquinolyl)sulfonyl]-1,3-propylenediamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

According to the method of Example 1, Step A, a solution of N-(3-aminopropyl)carbamic acid tert-butyl ester (383 mg) and triethylamine (335 μl) in dichloromethane (3 ml) was added with a solution of (1-chloro-5-isoquinolyl)sulfonyl chloride (524 mg, prepared from (1-chloro-5-isoquinolyl)sulfonyl chloride hydrochloride according to the method of Japanese Patent Unexamined Publication (Kokai) No. 63-2980) in dichloromethane (3 ml) with stirring and ice cooling and stirred at room temperature for 20 hours. The reaction mixture was successively washed with saturated aqueous sodium hydrogencarbonate twice and with saturated brine. The organic layer was dried over anhydrous sodium sulfate (Wako Pure Chemical Industries), and then the solvent was evaporated under reduced pressure. Then, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1) to obtain the title compound (640 mg).

Workup

  1. washThe reaction mixture was successively washed with saturated aqueous sodium hydrogencarbonate twice
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate (Wako Pure Chemical Industries)
  3. customthe solvent was evaporated under reduced pressure
  4. customThen, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-0b98f7d580184ebbb6b7dbce359be919
Source dataset
uspto-grants-2006_08
Patent number
US07094789B2

Linked notes

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