Triethylamine → HCID 58485258, compound

HRID 403589Notes

Reaction equation

HRID 403589 reaction equation
[CH3:1][C:2]([CH3:21])([CH3:20])[C@@H:3]([NH:5][CH2:6][CH2:7][C@:8]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)([NH2:12])[CH2:9][CH:10]=[CH2:11])[CH3:4].C(N(CC)CC)C.Cl[C:30](Cl)([O:32]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[CH2:9]([C@:8]1([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH2:7][CH2:6][N:5]([C@H:3]([C:2]([CH3:20])([CH3:1])[CH3:21])[CH3:4])[C:30](=[O:32])[NH:12]1)[CH:10]=[CH2:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 58485272HCID 58485272, compound

Product 1

HCID 58485258HCID 58485258, compoundYield 131.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)—N1—((S)-3,3-dimethylbutan-2-yl)-3-(4-fluorophenyl)hex-5-ene-1,3-diamine (600 mg, 2.05 mmol) and triethylamine (1.04 g, 10.25 mmol) in CH2Cl2 (10 mL) was added triphosgene (203 mg, 0.68 mmol) at 0° C., and the mixture was stirred for 2 h. The reaction was quenched with water, and the mixture was extracted with CH2Cl2. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to give the crude product, which was purified by preparative TLC to afford (R)-4-allyl-1-((S)-3,3-dimethylbutan-2-yl)-4-(4-fluorophenyl)tetrahydropyrimidin-2(1H)-one (285 mg, 44%). 1H NMR (CDCl3): 0.72 (s, 9H), 1.01 (d, 3H), 1.79 (m, 1H), 2.06 (m, 1H), 2.34 (m, 1H), 2.56 (m, 1H), 2.73 (m, 1H), 3.03 (m, 1H), 4.49 (m, 1H), 4.92 (5, 1H), 5.04-5.13 (m, 2H), 5.26 (m, 1H), 6.95-6.99 (m, 2H), 7.22-7.25 (m, 2H).

Workup

  1. customThe reaction was quenched with water
  2. extractionthe mixture was extracted with CH2Cl2
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product, which
  8. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-512bc9574d4648629f04aebc2a77f1cd
Source dataset
uspto-grants-2014_06
Patent number
US08748444B2

Reaction notes

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