Triethylamine → HCID 59627209, compound

HRID 1523241Notes

Reaction equation

HRID 1523241 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][CH2:11][CH2:12][C@:13]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)([NH2:17])[CH2:14][CH:15]=[CH2:16])[CH3:9])=[CH:4][CH:3]=1.CCN(CC)CC.Cl[C:33](Cl)([O:35]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[CH2:14]([C@:13]1([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[CH2:12][CH2:11][N:10]([C@H:8]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)[CH3:9])[C:33](=[O:35])[NH:17]1)[CH:15]=[CH2:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 59627251HCID 59627251, compound

Product 1

HCID 59627209HCID 59627209, compoundYield 20.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)—N1—((S)-1-(4-bromophenyl)ethyl)-3-(4-fluorophenyl)hex-5-ene-1,3-diamine (12 g, 31 mmol) in CH2Cl2 (100 mL) and Et3N (36 g, 0.36 mmol) was added triphosgene (3.50 g, 11.8 mmol) at 0° C. The resulting mixture was stirred for 3 h. The mixture was washed with water. The organic layer was separated, and concentrated to give the crude product, which was purified by column chromatography to afford (R)-4-allyl-1-((S)-1-(4-bromophenyl)ethyl)-4-(4-fluorophenyl)tetrahydropyrimidin-2(1H)-one (1.0 g, 8%). 1H NMR (CDCl3): δ=1.49 (t, 3H), 2.00 (m, 2H), 2.35 (m, 2H), 2.76 (m, 2H), 5.18 (m, 2H), 5.31 (m, 2H), 5.72 (q, 1H), 6.95 (m, 4H), 7.18 (m, 2H), 7.254 (m, 2H).

Workup

  1. washThe mixture was washed with water
  2. customThe organic layer was separated
  3. concentrationconcentrated
  4. customto give the crude product, which
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-5e965fa94fe54020a0cefa213f1b3914
Source dataset
uspto-grants-2015_07
Patent number
US09079861B2

Reaction notes

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