Triethylamine → HCID 178472925, compound

HRID 1957569Notes

Reaction equation

HRID 1957569 reaction equation
[C:1]([NH:7][C:8]1[N:9]=[C:10]([OH:20])[C:11]2[CH:17]=[C:16]([C:18]#[CH:19])[CH:15]=[N:14][C:12]=2[N:13]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH2:21]([O:23][C:24](=[O:36])[CH2:25][NH:26][S:27]([C:30]1[S:31][C:32](Br)=[CH:33][CH:34]=1)(=[O:29])=[O:28])[CH3:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>C(#N)C.[Pd](Cl)Cl>[CH2:21]([O:23][C:24](=[O:36])[CH2:25][NH:26][S:27]([C:30]1[S:31][C:32]([C:19]#[C:18][C:16]2[CH:15]=[N:14][C:12]3[N:13]=[C:8]([NH:7][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])[N:9]=[C:10]([OH:20])[C:11]=3[CH:17]=2)=[CH:33][CH:34]=1)(=[O:29])=[O:28])[CH3:22]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 19681623N-(5-bromothien-2-ylsulfonyl)glycine ethyl esterHCID 178437079HCID 178437079, compound

Product 1

HCID 178472925HCID 178472925, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 436 mg (1.27 mmol) of 2-pivaloylamino-4-hydroxy-6-ethynylpyrido[2,3-d]pyrimidine, 415 mg of N-(5-bromothien-2-ylsulfonyl)glycine ethyl ester, 20 mg of palladium chloride, 54 mg of triphenylphosphine, 10 mg of cuprous iodide, and 0.4 mL of triethylamine in 7 mL of acetonitrile was heated to reflux under nitrogen for 1 hour. The resulting reaction mixture was then concentrated in vacuo and the residue flash chromatographed with 4% CH3 OH/chloroform to give 610 mg of N-[5-(2-pivaloylamino-4-hydroxypyrido[2,3-d]pyrimidin-6-ylethynyl)thien-2-ylsulfonyl]glycine ethyl ester as a tan solid. 1H NMR (300 MHz, DMSO-d6) δ1.13 (t, J=7 Hz, 3H), 1.25, (s, 9H), 3.79 (d, J=5.8 Hz, 2H), 3.99 (q, J=7 Hz, 2H), 7.48 (d, J=3.6 Hz, 1H), 7.56 (d, J=3.6 Hz, 1H), 8.51 (s, 1H), 8.65 (t, J=5.8 Hz, 1H), 8.99 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen for 1 hour
  3. customThe resulting reaction mixture
  4. concentrationwas then concentrated in vacuo
  5. customthe residue flash chromatographed with 4% CH3 OH/chloroform

Sources & evidence

ORD record
ord-061d9dd359d74f2e838634bb75a3cb6c
Source dataset
uspto-grants-1998_07
Patent number
US05786358

Reaction notes

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