HCID 178418361, compound → HCID 178500485, compound

HRID 1108279Notes

Reaction equation

HRID 1108279 reaction equation
[C:1]([NH:7][C:8]1[N:9]=[C:10]([OH:58])[C:11]2[CH:17]=[C:16]([C:18]#[C:19][C:20]3[N:21](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:22]=[C:23]([C:25]([NH:27][C@H:28]([C:35]([O:37][CH3:38])=[O:36])[CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[O:26])[N:24]=3)[CH:15]=[N:14][C:12]=2[N:13]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[H][H]>[Pd].CO>[C:1]([NH:7][C:8]1[N:9]=[C:10]([OH:58])[C:11]2[CH2:17][CH:16]([CH2:18][CH2:19][C:20]3[NH:21][CH:22]=[C:23]([C:25]([NH:27][C@H:28]([C:35]([O:37][CH3:38])=[O:36])[CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[O:26])[N:24]=3)[CH2:15][NH:14][C:12]=2[N:13]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178500484HCID 178500484, compound

Product 1

HCID 178500485HCID 178500485, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of dimethyl N-{2-[2-(2-pivaloylamino-4-hydroxypyrido[2,3-d]-pyrimidin-6-yl)ethynyl]-1-triphenylmethylimidazol-4-ylcarbonyl}-L-glutamate (390 mg, 0.5 mmol) and 10% palladium-on-carbon catalyst (390 mg) in methanol (15 mL) was stirred under 50 psi of hydrogen for 7 days at room temperature. The workup was performed as described in Example 2 to yield 130 mg (48%) of dimethyl N-{2-[2-(2-pivaloylamino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]imidazol-4-ylcarbonyl}-L-glutamate as a pale yellow solid, mp 129-131° C.: 1H NMR (CDCl3) δ 11.35 (br s, 1H), 8.95 (br s, 1H), 7.54 (d, 1H, J=8.4 Hz), 7.49 (s, 1H), 4.75 (m, 1H), 3.69 (s, 3H), 3.60 (s, 3H), 3.30 (M, 1H), 2.87 (m, 1H), 2.80-2.60 (m, 3H), 2.43 (m, 2H), 2.27 (m, 1H), 2.15-1.92 (m, 2H), 1.80-1.60 (m, 3H), 1.26 (s, 9H).

Sources & evidence

ORD record
ord-57497f1717f94dde9aeba8435113cf74
Source dataset
uspto-grants-2000_05
Patent number
US06066639

Reaction notes

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