Ethylmorpholine → GW-842,166X

HRID 1868373Notes

Reaction equation

HRID 1868373 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(N1CCOCC1)C.[NH2:31][CH2:32][CH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[O:36]1[CH2:37][CH2:38][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])[CH2:34][CH2:35]1

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27732104-AminomethyltetrahydropyranHCID 27960291-Hydroxybenzotriazole hydrateHCID 16719743HCID 16719743, compound

Product 1

HCID 10253143GW-842,166XYield 88.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2,4-dichlorophenylamino)-4-trifluoromethyl-pyrimidine-5-carboxylic acid (30 mg) in dimethylformamide (2 ml) was added successively N-ethylmorpholine (33 μl), 4-aminomethyltetrahydropyran (12 mg), 1-hydroxybenzotriazole hydrate (18 mg) and 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide hydrochloride (20 mg). The solution was stirred for 3 h and allowed to stand overnight. Dimethylformamide was removed under reduced pressure and ethyl acetate (5 ml) added. The solution was washed sequentially with 5% sodium bicarbonate solution (2.5 ml), water (2.5 ml), 5% citric acid solution (2.5 ml) and brine (2×2.5 ml), dried (MgSO4) and evaporated to afford the title compound (34 mg) NMR (DMSO-d6) δ 1.20 (2H, m), 1.58 (2H, d), 1.70 (1H, m), 3.10 (2H, t), 3.23 (2H, t), 3.84 (2H, dd), 7.46 (1H, dd), 7.57 (1H, d), 7.71 (1H, d), 8.59 (1H, t), 8.63 (1H, s), 10.00 (1H, s).

Workup

  1. waitto stand overnight
  2. customDimethylformamide was removed under reduced pressure and ethyl acetate (5 ml)
  3. additionadded
  4. washThe solution was washed sequentially with 5% sodium bicarbonate solution (2.5 ml), water (2.5 ml), 5% citric acid solution (2.5 ml) and brine (2×2.5 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-9aa9a1e64b5542b48456d0488f411b09
Source dataset
uspto-grants-2009_12
Patent number
US07635701B2

Reaction notes

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