Ethylmorpholine → GW-842,166X

HRID 1868376Notes

Reaction equation

HRID 1868376 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[C:13]([C:20]([OH:22])=O)=[CH:12][N:11]=1.C(N1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)C.[NH2:31][CH2:32][CH:33]1CCCCO1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[O:28]1[CH2:27][CH2:26][CH:33]([CH2:32][NH:31][C:20]([C:13]2[C:14]([C:16]([F:17])([F:19])[F:18])=[N:15][C:10]([NH:9][C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])=[N:11][CH:12]=2)=[O:22])[CH2:30][CH2:29]1

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 97924(Tetrahydro-2H-pyran-2-ylmethyl)amineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 16719743HCID 16719743, compound

Product 1

HCID 10253143GW-842,166X

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2,4-dichlorophenylamino)-4-trifluoromethyl-pyrimidine-5-carboxylic acid (86 g) in dimethylformamide (800 ml) was added successively N-ethylmorpholine (93 ml), 4 aminomethyltetrahydropyran (29.5 g), 1-hydroxybenzotriazole hydrate (51.5 g) and 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide hydrochloride (56.2 g). The solution was stirred for 24 h. Dimethylformamide was partially removed (approx 650 ml) under reduced pressure and 5% sodium bicarbonate solution added (3×500 ml, added portionwise to control the release of carbon dioxide). The mixture was stirred with overhead stirring for 3 h and the resulting solid filtered onto a sinter. The solid was washed with 5% sodium bicarbonate (4×400 ml) and water (3×400 ml) then dried over sodium hydroxide in vacuo at 50° C. to afford the title compound (109.1 g)

Workup

  1. customDimethylformamide was partially removed (approx 650 ml) under reduced pressure and 5% sodium bicarbonate solution
  2. additionadded (3×500 ml
  3. additionadded portionwise
  4. stirringThe mixture was stirred with overhead
  5. stirringstirring for 3 h
  6. filtrationthe resulting solid filtered onto a sinter
  7. washThe solid was washed with 5% sodium bicarbonate (4×400 ml) and water (3×400 ml)
  8. dry with materialthen dried over sodium hydroxide in vacuo at 50° C.

Sources & evidence

ORD record
ord-f712f90e04fe47f0b67db628679cf36c
Source dataset
uspto-grants-2009_12
Patent number
US07635701B2

Reaction notes

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