Triethylamine → HCID 118271819, compound

HRID 590823Notes

Reaction equation

HRID 590823 reaction equation
[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH2:10][O:11][CH3:12])[N:5]=[C:4](Cl)[CH:3]=1.[C:14]1([C@H:20]([NH:22][C:23]([NH2:25])=[O:24])[CH3:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(N(CC)CC)C>C1COCC1>[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH2:10][O:11][CH3:12])[N:5]=[C:4]([NH:25][C:23]([NH:22][C@@H:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:21])=[O:24])[CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 13013340(R)-1-(1-phenylethyl)ureaHCID 118272362HCID 118272362, compound

Product 1

HCID 118271819HCID 118271819, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4,6-dichloro-2-(methoxymethyl)nicotinonitrile (75.7 mg, 0.349 mmol), (R)-1-(1-phenylethyl)urea (77 mg, 0.469 mmol) and Xantphos G2 (39 mg, 0.044 mmol) in THF (2 ml) was sealed, sparged with argon, charged with triethylamine (0.17 ml, 1.220 mmol) and heated to 50° C. for 17 hr. The mixture was cooled and filtered through celite, eluted with EtOAc before it was concentrated in vacuo and purified via flash chromatography (25-100% Et2O/hexane) to provide (R)-1-(4-chloro-5-cyano-6-(methoxymethyl)pyridin-2-yl)-3-(1-phenylethyl)urea. MS ESI calc'd for C17H18ClN4O2 [M+H]+ 345. found 345.

Workup

  1. customwas sealed
  2. customsparged with argon
  3. temperatureThe mixture was cooled
  4. filtrationfiltered through celite
  5. washeluted with EtOAc before it
  6. concentrationwas concentrated in vacuo
  7. custompurified via flash chromatography (25-100% Et2O/hexane)

Sources & evidence

ORD record
ord-32deadfe528941fca8d50a7a455535de
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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