4-Methylmorpholine → HCID 69780088, compound

HRID 1279090Notes

Reaction equation

HRID 1279090 reaction equation
[CH2:1]([O:3][C:4]([NH:6][C@@H:7]([C:18]([S:21][CH:22]([CH3:24])[CH3:23])([CH3:20])[CH3:19])[C:8]([N:10]1[CH2:14][CH2:13][CH2:12][C@H:11]1[C:15]([OH:17])=O)=[O:9])=[O:5])[CH3:2].[NH2:25][CH2:26][C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[C:33]([NH2:37])=[N:32][CH:31]=[CH:30]2.CN1CCOCC1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C)C=O.CC(O)=O>[CH2:1]([O:3][C:4](=[O:5])[NH:6][C@H:7]([C:8]([N:10]1[CH2:14][CH2:13][CH2:12][C@H:11]1[C:15](=[O:17])[NH:25][CH2:26][C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[C:33]([NH2:37])=[N:32][CH:31]=[CH:30]2)=[O:9])[C:18]([S:21][CH:22]([CH3:23])[CH3:24])([CH3:20])[CH3:19])[CH3:2]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 221697756-(Aminomethyl)isoquinolin-1-amineHCID 22958441HCID 22958441, compound

Product 1

HCID 69780088HCID 69780088, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-[2-(R)-ethoxycarbonylamino-3-isopropylsulfanyl-3-methyl-butyryl]-pyrrolidine-2-(S)-carboxylic acid (0.160 g), 6-aminomethyl-isoquinolin-1-ylamine (0.078 g), N-methyl morpholine (0.14 mL) and 0.14 g of 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU) in 3 mL of dry N,N-dimethyl formamide was stirred for 3 h at ambient temperature. 0.100 mL CH3COOH were added, the mixture was concentrated and the remaining residue was purified by HPLC (RP-18; H2O/CH3OH 95/5→0/100) to give 0.17 g (66%) of the title compound as a colorless oil. (+)-APCI-MS: 516 (MH+).

Workup

  1. concentrationthe mixture was concentrated
  2. customthe remaining residue was purified by HPLC (RP-18; H2O/CH3OH 95/5→0/100)

Sources & evidence

ORD record
ord-766b493261ca498da24dfd432ea96985
Source dataset
uspto-grants-2002_09
Patent number
US06444672B1

Reaction notes

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