Triethylamine → HCID 136050850, compound

HRID 2115723Notes

Reaction equation

HRID 2115723 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][NH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:6]([CH:15]2[CH2:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]2)[CH:5]=[C:4]([C:28]2[C:33]([OH:34])=[CH:32][CH:31]=[CH:30][C:29]=2[O:35][CH2:36][CH:37]2[CH2:39][CH2:38]2)[N:3]=1.C(N(CC)CC)C.Cl[C:48](Cl)([O:50]C(=O)OC(Cl)(Cl)Cl)Cl>O1CCCC1>[C:24]([O:23][C:21]([N:17]1[CH2:18][CH2:19][CH2:20][CH:15]([C:6]2[C:7]3[CH2:8][N:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:48](=[O:50])[NH:1][C:2]=3[N:3]=[C:4]([C:28]3[C:33]([OH:34])=[CH:32][CH:31]=[CH:30][C:29]=3[O:35][CH2:36][CH:37]3[CH2:38][CH2:39]3)[CH:5]=2)[CH2:16]1)=[O:22])([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 136050695HCID 136050695, compound

Product 1

HCID 136050850HCID 136050850, compoundYield 595.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (0° C.) solution of tert-butyl 3-(2-amino-6-[2-(cyclopropylmethoxy)-6-hydroxyphenyl]-3-{[(ethoxycarbonyl)amino]methyl}-4-pyridinyl)-1-piperidinecarboxylate (0.145 g, 0.268 mmol), which was obtained in the step (1) of Example 23-2, and triethylamine (0.226 mL, 1.609 mmol) in tetrahydrofuran (30 mL) was added triphosgene (0.079 g, 0.268 mmol) in tetrahydrofuran (10 mL) under an argon atmosphere. The mixture was allowed to warm to room temperature, and the stirring was continued for 3 hrs. After quenched by water, the mixture was extracted with ethyl acetate. The separated organic phase was washed with water and brine successively, dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting residue was purified by preparative TLC (hexane/ethyl acetate=1/1) to give ethyl 5-[1-(tert-butoxycarbonyl)-3-piperidinyl]-7-[2-(cyclopropylmethoxy)-6-hydroxyphenyl]-2-oxo-1,4-dihydropyrido[2,3-d]pyrimidine-3(2H)-carboxylate as a white solid (0.904 g, yield; 60%).

Workup

  1. customAfter quenched by water
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe separated organic phase was washed with water and brine successively
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by preparative TLC (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-297cc3be57c048b881b861a49452edb6
Source dataset
uspto-grants-2008_10
Patent number
US07435743B2

Reaction notes

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