4-Methylmorpholine → HCID 59428664, compound

HRID 504146Notes

Reaction equation

HRID 504146 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:9]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2[C:18]([OH:20])=O)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.[CH:21]1[CH:30]=[C:29]2[C:24]([CH:25]=[C:26]([NH:31][C:32]([C@@H:34]([NH2:45])[CH2:35][C:36]3[C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[NH:38][CH:37]=3)=[O:33])[CH:27]=[CH:28]2)=[CH:23][CH:22]=1.CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>ClCCl.CN(C1C=CN=CC=1)C>[NH:38]1[C:39]2[C:44](=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:36]([CH2:35][C@H:34]([NH:45][C:18]([C@@H:13]2[CH2:14][CH2:15][CH2:16][CH2:17][N:12]2[S:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)(=[O:10])=[O:11])=[O:20])[C:32](=[O:33])[NH:31][C:26]2[CH:27]=[CH:28][C:29]3[C:24](=[CH:23][CH:22]=[CH:21][CH:30]=3)[CH:25]=2)=[CH:37]1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 6761683326-63-4HCID 66750797HCID 66750797, compound

Product 1

HCID 59428664HCID 59428664, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.78 g (2.60 mmol) of (S)-1-(3-methoxy-benzenesulfonyl)-piperidine-2-carboxylic acid and 1.03 g (3.12 mmol) of (S)-2-amino-3-(1-indol-3-yl)-naphthalen-2-yl-propionamide in dichloromethane (100 ml) was added 0.16 g (1.30 mmol) DMAP followed by addition of 4-methylmorpholine 1.37 g (13.54 mmol), HOBT 0.84 g (6.25 mmol) and EDCI 1.39 g (7.29 mmol). The mixture was stirred at room temperature overnight. The reaction mixture was then washed with water, dried (sodium sulfate). Chromatography on silica gel eluting with 50% ethyl acetate/heptane proved 1.2 g (1.96 mmol) of the title compound. 1H NMR (300 MHz, CDCl3): 1.34-1.01 (m, 5H); 2.07 (bd, 1H); 2.21 (dd, 1H); 3.43-3.48 (m, 3H); 3.83 (s, 3H); 4.34 (b, 1H); 4.98 (q, 1H); 6.98 (d, 1H); 7.09-7.47 (m, 11H); 7.68-7.80 (m, 4H); 8.15 (s, 1H); 8.21 (s, 1H); 8.40 (s, 1H).

Workup

  1. washThe reaction mixture was then washed with water
  2. dry with materialdried (sodium sulfate)

Sources & evidence

ORD record
ord-4553f8d27fdd45b780deab444c3d3cdb
Source dataset
uspto-grants-2010_08
Patent number
US07777042B2

Reaction notes

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