HCID 178418681, compound → HCID 178500483, compound

HRID 2226019Notes

Reaction equation

HRID 2226019 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][C:31]([NH:33][C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36])=[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:11]=[CH:12][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:28][CH:29]=2)[CH:6]=[N:5][C:4]2=[N:30][C:31]([NH:33][C:34](=[O:39])[C:35]([CH3:37])([CH3:36])[CH3:38])=[CH:32][C:3]=12

Participants

5

Reactant 1

HCID 178418681HCID 178418681, compound

Product 1

HCID 178500483HCID 178500483, compoundYield 71.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.0 g of dimethyl N-[4-(4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidin-3-ylethynyl)benzoyl]-L-glutamate in 250 mL of 50% methanol in methylene chloride and 0.8 g of 3% palladium-on-carbon is hydrogenated at 50 p.s.i. for three hours, filtered, and concentrated under reduced pressure. The solid is collected by filtration and dried to yield 0.72 g of dimethyl N-{4-[2-(4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidin-3-yl)ethyl]benzoyl}-L-glutamate- mp 247° C. 1NMR (d6 -DMSO)δ1.21 (s, 9H), 1.90-2.12 (m, 2H), 2.42 (t, J=7.4 Hz, 2H), 2.92 (t, J=4 Hz, 2H), 2.97 (t, J=4 Hz, 2H), 3.55 (s, 3H), 3.61 (s, 3H), 4.38-4.45 (m, 1H), 6.61 (s, 1H), 7.27 (d, J=8.2 Hz, 2 H), 7.75 (d, J=8.2 Hz, 2 H), 8.64 (d, J=7.4 Hz, 1 H), 10.75 (s, 1H), 11.22 (s, 1H) . Anal. Calc. for C27H33N5O7 : C, 60.10; H 6.17; N, 12 . 98. Found: C, 59.94; H, 6.15; N, 12.72 .

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. filtrationThe solid is collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-445f99aeb4004b46a8e592520098b673
Source dataset
uspto-grants-1994_09
Patent number
US05344932

Reaction notes

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