Ethyl chloroformate → HCID 68672181, compound

HRID 571942Notes

Reaction equation

HRID 571942 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:44]=[C:45]([F:47])[CH:46]=1)[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[NH:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]2)=[CH:20][C:19]=1[NH:37][CH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1)=[O:17].[C:48](Cl)(=[O:52])[O:49][CH2:50][CH3:51]>O1CCCC1.ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:44]=[C:45]([F:47])[CH:46]=1)[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:48]([O:49][CH2:50][CH3:51])=[O:52])[N:10]=[C:9]2[NH:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:20][C:19]=1[NH:37][CH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1)=[O:17]

Participants

5

Reactant 2

HCID 10928Ethyl chloroformateHCID 68671750HCID 68671750, compound

Product 1

HCID 68672181HCID 68672181, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl 4-[4-{[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]carbamoyl}-3-(tetrahydro-2H-pyran-4-ylamino)phenyl]piperazine-1-carboxylate (0.013 mmol) in anhydrous tetrahydrofurane (1.0 mL) maintained at −50° C. under argon atmosphere a 1M solution of LiHMSD in anhydrous tetrahydrofurane (0.015 mL) was added. After stirring at that temperature for 5 minutes ethyl chlorocarbonate (0.002 mL, 1.63 mg, 0.015 mmol) was added. After 30 minutes at −50° C. the reaction was completed. After diluting with dichloromethane, the solution was washed with brine, dried over sodium sulphate and evaporated to dryness. The crude was dissolved in dichloromethane (1 mL), trifluoroacetic acid (0.1 mL) was added and the mixture was stirred at room temperature overnight. After diluting with dichloromethane, the solution was washed with sodium hydrogencarbonate, with brine, dried over sodium sulphate and evaporated to dryness.

Workup

  1. additionwas added
  2. additionwas added
  3. washthe solution was washed with brine
  4. dry with materialdried over sodium sulphate
  5. customevaporated to dryness
  6. dissolutionThe crude was dissolved in dichloromethane (1 mL)
  7. additiontrifluoroacetic acid (0.1 mL) was added
  8. additionAfter diluting with dichloromethane
  9. washthe solution was washed with sodium hydrogencarbonate, with brine
  10. dry with materialdried over sodium sulphate
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-da252c100df04565bed72dea914ec3f7
Source dataset
uspto-grants-2015_05
Patent number
US09029356B2

Reaction notes

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