Triethylamine → HCID 136050731, compound

HRID 412299Notes

Reaction equation

HRID 412299 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][NH:9][C:10]([NH:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:11])=[C:6]([CH:19]2[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:20]2)[CH:5]=[C:4]([C:32]2[C:37]([OH:38])=[CH:36][CH:35]=[CH:34][C:33]=2[O:39][CH2:40][CH:41]2[CH2:43][CH2:42]2)[N:3]=1.C(N(CC)CC)C.Cl[C:52](Cl)([O:54]C(=O)OC(Cl)(Cl)Cl)Cl>O1CCCC1>[CH:13]1([NH:12][C:10]([N:9]2[CH2:8][C:7]3[C:6]([CH:19]4[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:20]4)=[CH:5][C:4]([C:32]4[C:37]([OH:38])=[CH:36][CH:35]=[CH:34][C:33]=4[O:39][CH2:40][CH:41]4[CH2:43][CH2:42]4)=[N:3][C:2]=3[NH:1][C:52]2=[O:54])=[O:11])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 135550612HCID 135550612, compound

Product 1

HCID 136050731HCID 136050731, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of tert-butyl 3-{2-amino-3-({[(cyclohexylamino)-carbonyl]amino}methyl)-6-[2-(cyclopropylmethoxy)-6-hydroxyphenyl]-4-pyridinyl}-1-piperidinecarboxylate(0.039 g, 0.065 mmol), which was obtained in the step (1) of Example 23-3, and triethylamine (15.0 mL, 0.389 mmol) in tetrahydrofuran (10.0 mL) was added dropwise a solution of triphosgene (0.019 g, 0.065 mmol) in tetrahydrofuran (5.0 mL) under an argon atmosphere. The mixture was stirred at 0° C. for 2 hrs. After quenched by water, the mixture was extracted with ethyl acetate. The separated organic phase was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The resulting residue (white solid) was triturated with diisopropyl ether, collected by filtration, washed with diisopropyl ether, and dried under reduced pressure to give tert-butyl 3-{3-[(cyclohexylamino)carbonyl]-7-[2-(cyclopropylmethoxy)-6-hydroxyphenyl]-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidin-5-yl}-1-piperidinecarboxylate (0.021 g, yield; 52%).

Workup

  1. customAfter quenched by water
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe separated organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue (white solid) was triturated with diisopropyl ether
  8. filtrationcollected by filtration
  9. washwashed with diisopropyl ether
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-3ef12a9f3e2041318a4463cd14c91cf6
Source dataset
uspto-grants-2003_05
Patent number
US06562811B1

Reaction notes

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