HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Triethylamine → HCID 178471562, compound

HRID 22023
Notes
Print preview

Reaction equation

HRID 22023 reaction equation
[OH:1][C:2]1[C:3]2[C:17]([C:18]#[CH:19])=[CH:16][NH:15][C:4]=2[N:5]=[C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[N:7]=1.[CH2:20]([O:22][C:23](=[O:42])[C@H:24]([CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[NH:25][C:26](=[O:34])[C:27]1[CH:32]=[CH:31][C:30](I)=[CH:29][CH:28]=1)[CH3:21].C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C.[Pd](Cl)Cl.O>[CH2:20]([O:22][C:23](=[O:42])[C@H:24]([CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[NH:25][C:26](=[O:34])[C:27]1[CH:28]=[CH:29][C:30]([C:19]#[C:18][C:17]2[C:3]3[C:2]([OH:1])=[N:7][C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[N:5][C:4]=3[NH:15][CH:16]=2)=[CH:31][CH:32]=1)[CH3:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 1885228diethyl (2S)-2-[(4-iodobenzoyl)amino]pentanedioateHCID 178437174HCID 178437174, compound

Product 1

HCID 178471562HCID 178471562, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 24290
Palladium Chloride
Catalyst
HCID 962WaterSolvent
HCID 6342AcetonitrileSolvent2×

Procedure

To a suspension of 3.33 g (12.9 mmol) of N-(4-hydroxy-5-ethynyl-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide in 64 mL of acetonitrile stirred under nitrogen was added 5.77 g (28.4 mmol) of BSA and the resulting mixture was stirred at 40° C. for 2 hours, then cooled to ambient temperature. To the resulting solution was added sequentially 5.58 g (12.9 mmol) of N-4-iodobenzoyl-L-glutamic acid diethyl ester, 2.6 g (25.8 mmol) of triethylamine, and a mixture of 0.114 g (0.65 mmol) of palladium(II) chloride and 0.338 g (1.29 mmol) of triphenylphosphine in 16 mL of acetonitrile. The resulting mixture was heated under reflux overnight (18 hours), after which time HPLC analysis of an aliquot indicated complete conversion of the (acetylenic) starting material. The mixture was cooled to ambient temperature and 2 mL of water was added. The resulting suspension was stirred for 30 minutes, filtered, and the precipitate washed with acetonitrile and dried, affording 6.15 g (85%) of N-[4-[2-[2-(2,2-dimethylpropionyl)amino-4-hydroxy-7H-pyrrolo[2,3-d]pyrimidin-5-yl ]ethynyl]benzoyl]-L-glutamic acid diethyl ester as a tan solid. The melting point and NMR spectral data for the product were in agreement with data obtained on an authentic sample prepared by the procedure of Example 3.

Workup

  1. additionwas added 5.77 g (28.4 mmol) of BSA
  2. stirringthe resulting mixture was stirred at 40° C. for 2 hours
  3. temperatureThe resulting mixture was heated
  4. temperatureunder reflux overnight (18 hours)
  5. temperatureThe mixture was cooled to ambient temperature
  6. stirringThe resulting suspension was stirred for 30 minutes
  7. filtrationfiltered
  8. washthe precipitate washed with acetonitrile
  9. customdried

Sources & evidence

ORD record
ord-284b254b09ae4d3e9cdfeff64dbfd8a2
Source dataset
uspto-grants-1995_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05426187

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes