Triethylamine → HCID 22258948, compound

HRID 1767408Notes

Reaction equation

HRID 1767408 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([NH:10][CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:5]=[C:4]([C:21]2[C:26]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)=[CH:25][CH:24]=[CH:23][C:22]=2[O:37][CH2:38][CH:39]2[CH2:41][CH2:40]2)[N:3]=1.CCN(CC)CC.Cl[C:50](Cl)([O:52]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1>[CH:39]1([CH2:38][O:37][C:22]2[CH:23]=[CH:24][CH:25]=[C:26]([O:27][CH2:28][C:29]3[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=3)[C:21]=2[C:4]2[CH:5]=[C:6]([NH:10][CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:19])[CH3:17])[C:7]3[CH2:8][O:9][C:50](=[O:52])[NH:1][C:2]=3[N:3]=2)[CH2:40][CH2:41]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 22258729HCID 22258729, compound

Product 1

HCID 22258948HCID 22258948, compoundYield 138.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) solution of tert-butyl 2-{[2-amino-6-{2-(cyclopropylmethoxy)-6-[(4-methoxybenzyl)oxy]phenyl}-3-(hydroxymethyl)-4-pyridinyl]amino}ethylcarbamate (0.050 g, 0.089 mmol) and Et3N (0.074 mL, 0.531 mmol) in THF (10 mL) was added triphosgene (0.013 g, 0.044 mmol) in one portion. The mixture was stirred at 0° C. for 1 hr, and then partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification by column chromatography on silica gel (ethyl acetate) gave tert-butyl 2-[(7-{2-(cyclopropylmethoxy)-6-[(4-methoxybenzyl)-oxy]phenyl}-2-oxo-1,4-dihydro-2H-pyrido[2,3-d][1,3]oxazin-5-yl)amino]ethylcarbamate as colorless oil (0.036 g, yield; 69%).

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by column chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-1ff728e7e4114454a1b107ed65bc82ab
Source dataset
uspto-grants-2007_06
Patent number
US07232909B2

Reaction notes

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