Triethylamine → HCID 136050683, compound

HRID 1611199Notes

Reaction equation

HRID 1611199 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[C:6]([CH:14]2[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]2)[CH:5]=[C:4]([C:27]2[C:32]([OH:33])=[CH:31][CH:30]=[CH:29][C:28]=2[O:34][CH2:35][CH:36]2[CH2:38][CH2:37]2)[N:3]=1.C(N(CC)CC)C.Cl[C:47](Cl)([O:49]C(=O)OC(Cl)(Cl)Cl)Cl>O1CCCC1>[CH:36]1([CH2:35][O:34][C:28]2[CH:29]=[CH:30][CH:31]=[C:32]([OH:33])[C:27]=2[C:4]2[CH:5]=[C:6]([CH:14]3[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]3)[C:7]3[CH2:8][N:9]([S:10]([CH3:13])(=[O:11])=[O:12])[C:47](=[O:49])[NH:1][C:2]=3[N:3]=2)[CH2:37][CH2:38]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 136050709HCID 136050709, compound

Product 1

HCID 136050683HCID 136050683, compoundYield 55%

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-{[(methylsulfonyl)amino]methyl}-4-pyridinyl)-1-piperidinecarboxylate (0.050 g, 0.091 mmol) and triethylamine (0.077 mL, 0.549 mmol) in tetrahydrofuran (15 mL) was added to a solution of triphosgene (0.027 g, 0.091 mmol) in tetrahydrofuran (5 mL) under an argon atmosphere. The mixture was allowed to warm to room temperature, and the stirring was continued for 3 hrs under an argon atmosphere. 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 yellow solid was triturated with diisopropyl ether and collected by filtration to give tert-butyl 3-[7-[2-(cyclopropylmethoxy)-6-hydroxyphenyl]-3-(methylsulfonyl)-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidin-5-yl]-1-piperidinecarboxylate as a yellow solid (0.028 g, yield; 55%).

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 yellow solid was triturated with diisopropyl ether
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-e4878911ec1042f7a3065f0d89975d32
Source dataset
uspto-grants-2006_01
Patent number
US06984649B1

Reaction notes

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