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

HRID 10490

Reaction equation

HRID 10490 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][NH2:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH:20]1[C:29]2[CH:28]=[CH:27][CH:26]=[C:25]([S:30](Cl)(=[O:32])=[O:31])[C:24]=2[CH:23]=[CH:22][N:21]=1>ClCCl>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][S:30]([C:25]1[CH:26]=[CH:27][CH:28]=[C:29]2[C:24]=1[CH:23]=[CH:22][N:21]=[CH:20]2)(=[O:31])=[O:32])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 33716555-Isoquinolinesulfonyl chloride

Product 1

HCID 21979958N-(tert-butoxycarbonyl)-N'-[(5-isoquinolyl)sulfonyl]-1,3-propylenediamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of N-(tert-butoxycarbonyl)-1,3-propylenediamine (2.09 g, Tokyo Kasei Kogyo) and triethylamine (3.4 ml, Tokyo Kasei Kogyo) in dichloromethane (20 ml) was added with a solution of isoquinoline-5-sulfonyl chloride (2.73 g, prepared according to Japanese Patent Unexamined Publication (Kokai) No. 61-227581) in dichloromethane (15 ml) with stirring and ice cooling and stirred at room temperature for 14 hours and 30 minutes. The reaction mixture was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure. Then, the residue was purified by flash column chromatography (chloroform:methanol=50:1) to obtain the title compound (4 g).

Workup

  1. customprepared
  2. washThe reaction mixture was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine
  3. customThe organic layer was dried
  4. customthe solvent was evaporated under reduced pressure
  5. customThen, the residue was purified by flash column chromatography (chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-e7e86c6093174ea1bac2f28462d3f752
Source dataset
uspto-grants-2006_08
Patent number
US07094789B2

Linked notes

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