4-Methylmorpholine → HCID 67343031, compound

HRID 1669312Notes

Reaction equation

HRID 1669312 reaction equation
[CH3:1][C:2]([CH3:33])([CH3:32])[CH2:3][CH2:4][CH:5]([C:16]1[CH:17]=[N:18][C:19]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)=[CH:20][CH:21]=1)[O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](O)=[O:12])=[CH:9][CH:8]=1.ClC1C(OC)=NN=NC=1OC.CN1CCOCC1.[CH3:52][O:53][C:54](=[O:59])[CH2:55][CH:56]([NH2:58])[CH3:57]>C(Cl)Cl.O>[CH3:52][O:53][C:54](=[O:59])[CH2:55][CH:56]([NH:58][C:11](=[O:12])[C:10]1[CH:9]=[CH:8][C:7]([O:6][CH:5]([C:16]2[CH:17]=[N:18][C:19]([C:22]3[CH:23]=[CH:24][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:27]=3)=[CH:20][CH:21]=2)[CH2:4][CH2:3][C:2]([CH3:1])([CH3:33])[CH3:32])=[CH:15][CH:14]=1)[CH3:57]

Participants

7

Reactant 4

HCID 79724-Methylmorpholine2×HCID 12493616Chloro-dimethoxy-triazineHCID 12500430Methyl 3-aminobutanoateHCID 673429454-{4,4-Dimethyl-1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-pentyloxy}-benzoic acid

Product 1

HCID 67343031HCID 67343031, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The 4-{4,4-Dimethyl-1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-pentyloxy}-benzoic acid (95 mg, 0.21 mmol), chloro-dimethoxy-triazine (CDMT) (37 mg, 0.21 mmol), and 4-methylmorpholine (25 uL, 0.23 mmol) are combined in anhydrous DCM under nitrogen. The reaction is allowed to stir under nitrogen at room temperature overnight. 3-Amino-butyric acid methyl ester (26 mg, 0.23 mmol) and 4-methylmorpholine (50 uL, 0.47 mmol) is then added to the reaction mixture, and allowed to stir at room temperature. Some water (<10% volume) is added to help solubility. The reaction is monitored by HPLC, and upon complete consumption of the acid, the reaction is diluted with DCM and water and rinsed with 1N HCl. The organic layer is washed with water and brine, dried over anhydrous sodium sulfate, then filtered and concentrated. The 3-(4-{4,4-dimethyl-1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-pentyloxy}-benzoylamino)-butyric acid methyl ester is isolated after column chromatography.

Workup

  1. stirringto stir at room temperature
  2. customupon complete consumption of the acid
  3. additionthe reaction is diluted with DCM and water
  4. washrinsed with 1N HCl
  5. washThe organic layer is washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b3954580d806457aa5b946ca7e5dff7c
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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