Triethylamine → HCID 118272458, compound

HRID 590820Notes

Reaction equation

HRID 590820 reaction equation
[C:1]([O:4][CH2:5][C:6]1[C:11]([C:12]#[N:13])=[C:10]([Cl:14])[CH:9]=[C:8](Cl)[N:7]=1)(=[O:3])[CH3:2].[C:16]1([C@H:22]([NH:24][C:25]([NH2:27])=[O:26])[CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=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>[C:1]([O:4][CH2:5][C:6]1[C:11]([C:12]#[N:13])=[C:10]([Cl:14])[CH:9]=[C:8]([NH:27][C:25]([NH:24][C@@H:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:23])=[O:26])[N:7]=1)(=[O:3])[CH3:2]

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 118271831HCID 118271831, compound

Product 1

HCID 118272458HCID 118272458, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of (4,6-dichloro-3-cyanopyridin-2-yl)methyl acetate (366.3 mg, 1.495 mmol), (R)-1-(1-phenylethyl)urea (443 mg, 2.70 mmol) and Xantphos G2 precatalyst (130 mg, 0.146 mmol) in THF (2 ml) was sealed, sparged with argon, charged with triethylamine (0.73 ml, 5.24 mmol) and heated to 50° C. for 17 hr. The mixture was filtered through celite, eluted with EtOAc, concentrated in vacuo and purified via flash chromatography (25-100% Et2O/Hex) to provide (R)-(4-chloro-3-cyano-6-(3-(1-phenylethyl)ureido)pyridin-2-yl)methyl acetate. MS ESI calc'd. For C18H18ClN4O3 [M+H]+ 373. found 373.

Workup

  1. customwas sealed
  2. customsparged with argon
  3. filtrationThe mixture was filtered through celite
  4. washeluted with EtOAc
  5. concentrationconcentrated in vacuo
  6. custompurified via flash chromatography (25-100% Et2O/Hex)

Sources & evidence

ORD record
ord-01d4e247dd3f4fb6ae5e5ed695468867
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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