Triethylamine → (S)-6-{3-(tert-butoxycarbonylamino)pyrrolidin-1-ylsulfonyl}isoquinoline

HRID 1845953Notes

Reaction equation

HRID 1845953 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[N:10][CH:9]=[CH:8]2)(=[O:4])=[O:3].Cl.Cl.N[C@@H]1CCN(S(C2C=C3C(=CC=2)C=NC=C3)(=O)=O)C1.[C:36]([O:40][C:41]([NH:43][C@H:44]1[CH2:48][CH2:47][NH:46][CH2:45]1)=[O:42])([CH3:39])([CH3:38])[CH3:37].C(N(CC)CC)C>ClCCl>[C:36]([O:40][C:41]([NH:43][C@H:44]1[CH2:48][CH2:47][N:46]([S:2]([C:5]2[CH:6]=[C:7]3[C:12](=[CH:13][CH:14]=2)[CH:11]=[N:10][CH:9]=[CH:8]3)(=[O:4])=[O:3])[CH2:45]1)=[O:42])([CH3:39])([CH3:37])[CH3:38]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 55280287Isoquinoline-6-sulfonyl chlorideHCID 66727170(R)-6-(3-aminopyrrolidin-1-ylsulfonyl)isoquinoline dihydrochloride

Product 1

HCID 66727094(S)-6-{3-(tert-butoxycarbonylamino)pyrrolidin-1-ylsulfonyl}isoquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A dichloromethane solution (100 mL) of 6-chlorosulfonylisoquinoline (Reference Compound 2) was added with stirring at room temperature to a solution containing 423 mg of (S)-(−)-3-(tert-butoxycarbonylamino)pyrrolidine dissolved in 20 mL of dichloromethane further supplemented with 0.5 mL of triethylamine, and reacted for 6 hour. The reaction solution was washed with saturated saline and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated, and the obtained crude product was purified by silica gel column chromatography (acetone:hexane=1:2) to obtain 560 mg of the compound of interest as a colorless oil (65%).

Workup

  1. customreacted for 6 hour
  2. washThe reaction solution was washed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated
  6. customthe obtained crude product
  7. customwas purified by silica gel column chromatography (acetone:hexane=1:2)

Sources & evidence

ORD record
ord-de958c0ddf41474598828c5ca6db4c47
Source dataset
uspto-grants-2015_02
Patent number
US08951997B2

Reaction notes

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