4-Methylmorpholine → N-(1-Amino-isoquinolin-6-ylmethyl)-1-tert.butoxycarbonyl-prolinamide

HRID 1279125Notes

Reaction equation

HRID 1279125 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][NH2:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[C:14]([N:21]1[CH2:28][CH2:27][CH2:26][C@H:22]1[C:23](O)=[O:24])([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][NH:13][C:23](=[O:24])[C@@H:22]3[CH2:26][CH2:27][CH2:28][N:21]3[C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 221697756-(Aminomethyl)isoquinolin-1-amine

Product 1

HCID 22958562N-(1-Amino-isoquinolin-6-ylmethyl)-1-tert.butoxycarbonyl-prolinamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.00 g of 1-Amino-6-aminomethyl-isoquinoline and 6.20 Boc-L-proline were dissolved in 88 mL DMF. 10.6 g of TBTU was added followed by a dropwise addition of N-methylmorpholine. Stirring was continued for 1 h at ambient temperature and the solvent was removed i.vac. The residue was extracted with 5% aqueous NaHCO3 solution and with ethyl acetate. The organic layer was separated and dried (NaSO4). The solvent was removed to give 10.7 g (quant.) of N-(1-Amino-isoquinolin-6-ylmethyl)-1-tert.butoxycarbonyl-prolinamide as an oil.

Workup

  1. customthe solvent was removed i.vac
  2. extractionThe residue was extracted with 5% aqueous NaHCO3 solution and with ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried (NaSO4)
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-6cc1ac40b849446b89276f52e4b31c61
Source dataset
uspto-grants-2002_09
Patent number
US06444672B1

Reaction notes

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