4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → HCID 49806037, compound

HRID 576887Notes

Reaction equation

HRID 576887 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([N:20]([CH3:37])[NH:21][C:22](=[O:36])[CH2:23][CH2:24][NH:25][C:26]([NH:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[C:17]([OH:19])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:38]([O:40][CH:41]([O:55][CH2:56][CH3:57])[CH2:42][NH:43][CH2:44][C:45]1[C:54]2[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=2)[CH:48]=[CH:47][CH:46]=1)[CH3:39].C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>ClCCl.C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C@H:16]([N:20]([CH3:37])[NH:21][C:22](=[O:36])[CH2:23][CH2:24][NH:25][C:26]([NH:28][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[O:27])[C:17]([N:43]([CH2:42][CH:41]([O:40][CH2:38][CH3:39])[O:55][CH2:56][CH3:57])[CH2:44][C:45]2[C:54]3[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=3)[CH:48]=[CH:47][CH:46]=2)=[O:19])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 53411263HCID 53411263, compoundHCID 66644546HCID 66644546, compound

Product 1

HCID 49806037HCID 49806037, compoundYield 44.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-3-(4-(benzyloxy)phenyl)-2-(2-(3-(3-benzylureido)propanoyl)-1-methylhydrazinyl)propanoic acid (Compound VII-1) 126 mg (0.25 mmol) in dichloromethane 1.5 ml, 2,2-diethoxy-N-(naphthalen-1-ylmethyl)ethanamine (Compound IV-2) 85 mg (0.31 mmol) and DMT-MM 173 mg (0.63 mmol) were added and the mixture was stirred at room temperature for 3 hr. The reaction mixture was diluted with chloroform 50 ml and washed with water 50 ml twice and brine 50 ml twice and dried over magnesium sulfate and filtered. The mother solution was concentrated in vacuo and the residue was purified on silica gel column chromatography (Merck 60N spherical, neutral 10 ml elution by chloroform:methanol=100:0 to 90:10, each elution 50 ml) to give the desired product as pale yellow oil 85.0 mg (35.8%).

Workup

  1. washwashed with water 50 ml twice
  2. dry with materialbrine 50 ml twice and dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe mother solution was concentrated in vacuo
  5. customthe residue was purified on silica gel column chromatography (Merck 60N spherical
  6. washneutral 10 ml elution by chloroform
  7. washmethanol=100:0 to 90:10, each elution 50 ml)

Sources & evidence

ORD record
ord-8fda5ffcc2eb4998b6756fe0ccb320b4
Source dataset
uspto-grants-2015_05
Patent number
US09040531B2

Reaction notes

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