Dimethylamine → HCID 68685733, compound

HRID 1865469Notes

Reaction equation

HRID 1865469 reaction equation
Cl[C:2]1[N:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:3]=1[C:4]([NH:6][CH2:7][C:8]1([CH2:21][CH:22]2[CH2:24][CH2:23]2)[CH2:13][CH2:12][CH:11]([S:14]([CH2:17][CH:18]2[CH2:20][CH2:19]2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=[O:5].O1CCCC1.[CH3:38][NH:39][CH3:40]>>[CH:18]1([CH2:17][S:14]([CH:11]2[CH2:12][CH2:13][C:8]([CH2:7][NH:6][C:4](=[O:5])[C:3]3[CH:25]=[CH:26][C:27]([C:29]([F:32])([F:31])[F:30])=[N:28][C:2]=3[N:39]([CH3:40])[CH3:38])([CH2:21][CH:22]3[CH2:24][CH2:23]3)[CH2:9][CH2:10]2)(=[O:16])=[O:15])[CH2:20][CH2:19]1

Participants

4

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 86609534HCID 86609534, compound

Product 1

HCID 68685733HCID 68685733, compoundYield 96%

Conditions

Temperature
70 °C

Procedure

2-Chloro-N-(4-cyclopropylmethanesulfonyl-1-cyclopropylmethylcyclohexylmethyl)-6-trifluoromethylnicotinamide (50 mg, 0.10 mmol) was dissolved in 2M dimethylamine in tetrahydrofuran (2 ml, 4 mmol) and heated in a sealed tube at 70° C. for 2 hours. The mixture was allowed to cool to ambient temperature then evaporated. The residue was purified by preparative plate chromatography eluting with 10% ethyl acetate in dichloromethane. Collecting the appropriate band, followed by trituration of the silica with ethyl acetate, filtration and evaporation gave a white foam (49 mg, 96%). 1H NMR δ (ppm)(CDCl3): 8.18 (1H, d, J=7.7 Hz), 7.65 (1H, s), 7.26 (1H, d, J=7.7 Hz), 3.63 (2H, d, J=6.2 Hz), 2.94-2.89 (9H, m), 2.07-1.81 (6H, m), 1.39-1.31 (2H, m), 1.28-1.14 (3H, m), 0.79-0.67 (3H, m), 0.55-0.49 (2H, m), 0.42 (2H, q, J=5.3 Hz), 0.06 (2H, t, J=4.2 Hz). MS (m/e)=503.

Workup

  1. temperatureto cool to ambient temperature
  2. customthen evaporated
  3. customThe residue was purified by preparative plate chromatography
  4. washeluting with 10% ethyl acetate in dichloromethane
  5. customCollecting the appropriate band
  6. filtrationfollowed by trituration of the silica with ethyl acetate, filtration and evaporation

Sources & evidence

ORD record
ord-e6d6d7e4f7864bbb9554f6498395862c
Source dataset
uspto-grants-2009_12
Patent number
US07626056B2

Reaction notes

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