Morpholine → HCID 67287001, compound

HRID 922022Notes

Reaction equation

HRID 922022 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][CH2:9][CH3:10])[C:5]([C:11]([O:13][CH3:14])=[O:12])=[C:4]([C:15]([F:18])([F:17])[F:16])[CH:3]=1.C(SC1C(C(OC)=O)=C(C(F)(F)F)C=C(SCC)N=1)C.[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1.CCN(C(C)C)C(C)C>CC#N.O.CCOC(C)=O>[CH2:9]([S:8][C:6]1[C:5]([C:11]([O:13][CH3:14])=[O:12])=[C:4]([C:15]([F:18])([F:17])[F:16])[CH:3]=[C:2]([N:39]2[CH2:44][CH2:43][O:42][CH2:41][CH2:40]2)[N:7]=1)[CH3:10]

Participants

8

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 67288028HCID 67288028, compoundHCID 86664318HCID 86664318, compound

Product 1

HCID 67287001HCID 67287001, compoundYield 16%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A solution of 2 g of a ˜1:1 mixture of methyl 6-chloro-2-(ethylsulfanyl)-4-(trifluoromethyl)-pyridine-3-carboxylate and methyl 2,6-bis(ethylsulfanyl)-4-(trifluoromethyl)-pyridine-3-carboxylate, 1.7 ml (20.0 mmol) morpholine and 3.5 ml (20.0 mmol) DIPEA in MeCN (10 ml) was heated in the microwave to 150° C. for 4 h. The RM was then diluted with water and EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 4:1) provided 440 mg (1.3 mmol, 16% over 2 steps) methyl 2-(ethylsulfanyl)-6-morpholin-4-yl-4-(trifluoromethyl)-pyridine-3-carboxylate.

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by CC (hexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-16ad6f99a2834f5fb83214103e01a9e8
Source dataset
uspto-grants-2016_03
Patent number
US09278103B2

Reaction notes

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