Triethylamine → HCID 22258948, compound

HRID 412323Notes

Reaction equation

HRID 412323 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}ethyl-carbamate (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-b7042e0da7d7480a9fbd482444b00afb
Source dataset
uspto-grants-2003_05
Patent number
US06562811B1

Reaction notes

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