HCID 178500481, compound → HCID 178500482, compound

HRID 982317Notes

Reaction equation

HRID 982317 reaction equation
[OH:1][C:2]1[N:7]([C:8]#[C:9][C:10]2[CH:29]=[CH:28][C:13]([C:14]([NH:16][C@H:17]([C:24]([O:26][CH3:27])=[O:25])[CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[O:15])=[CH:12][CH:11]=2)[CH:6]=[N:5][C:4]2=[N:30][CH:31]=[CH:32][C:3]=12>CO.C(Cl)Cl.[Pd]>[OH:1][C:2]1[N:7]([CH2:8][CH2:9][C:10]2[CH:29]=[CH:28][C:13]([C:14]([NH:16][C@H:17]([C:24]([O:26][CH3:27])=[O:25])[CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[O:15])=[CH:12][CH:11]=2)[CH:6]=[N:5][C:4]2=[N:30][CH:31]=[CH:32][C:3]=12

Participants

5

Reactant 1

HCID 178500481HCID 178500481, compound

Product 1

HCID 178500482HCID 178500482, compoundYield 60.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.1 g of dimethyl N-[4-(4-hydroxypyrrolo[2,3-d]pyrimidin-3-ylethynyl)benzoyl]-L-glutamate in 100 mL of 50% methanol in methylene chloride and 0.8 g of 3% palladium-on-carbon is hydrogenated at 50 p.s.i. for 24 hours, filtered, and concentrated under reduced pressure. Ether is added to the residue and the solid is collected by filtration and dried to yield 0.67 g of dimethyl N-{4-[2-(4-hydroxypyrrolo[2,3-d]pyrimidin-3-yl)ethyl]benzoyl}-L-glutamate. mp 170-172° C. 1NMR (d6 -DMSO) δ1.94-2.14 (m, 2H), 2.44 (t, J=7.4 Hz, 2H), 2.93-3.02 (m, 2H), 3.57 (s, 3H), 3.63 (s, 3H), 4.40-4.70 (m, 1H), 6.71 (s, 1H), 7.29 (d, J=8.2 Hz, 2 H), 7.77 (m, 3 H), 8.66 (d, J=7.4 Hz, 1H), 11.52 (s, 1H), 11.71 (s, 1H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. additionEther is added to the residue
  4. filtrationthe solid is collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-413ae2af0e18455ea8d139703fb1d301
Source dataset
uspto-grants-1991_02
Patent number
US04996206

Reaction notes

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