HCID 178472925, compound → HCID 178472926, compound

HRID 1957570Notes

Reaction equation

HRID 1957570 reaction equation
[CH2:1]([O:3][C:4](=[O:35])[CH2:5][NH:6][S:7]([C:10]1[S:11][C:12]([C:15]#[C:16][C:17]2[CH:34]=[N:33][C:20]3[N:21]=[C:22]([NH:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])[N:23]=[C:24]([OH:25])[C:19]=3[CH:18]=2)=[CH:13][CH:14]=1)(=[O:9])=[O:8])[CH3:2]>C(O)(=O)C.[Pt]=O>[CH2:1]([O:3][C:4](=[O:35])[CH2:5][NH:6][S:7]([C:10]1[S:11][C:12]([CH2:15][CH2:16][CH:17]2[CH2:34][NH:33][C:20]3[N:21]=[C:22]([NH:26][C:27](=[O:32])[C:28]([CH3:29])([CH3:30])[CH3:31])[N:23]=[C:24]([OH:25])[C:19]=3[CH2:18]2)=[CH:13][CH:14]=1)(=[O:8])=[O:9])[CH3:2]

Participants

4

Reactant 1

HCID 178472925HCID 178472925, compound

Product 1

HCID 178472926HCID 178472926, compoundYield 31.5%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)Catalyst2×HCID 176Acetic AcidSolvent

Procedure

To a mixture of 150 mg of N-[5-(2-pivaloylamino-4-hydroxypyrido[2,3-d]pyrimidin-6-ylethynyl)thien-2-ylsulfonyl]glycine ethyl ester in 25 mL of glacial acetic acid was added 100 mg of platinum oxide. This mixture was stirred under hydrogen for 24 hours and an additional 100 mg of platinum oxide was added. The hydrogenation was resumed for another 24 hours and the reaction mixture was then filtered through Celite® and the filtrate concentrated in vacuo. The residue was flash chromatographed on silica gel using 3.5% CH3OH and chloroform to give 48 mg of N-{5-[2-(2-pivaloylamino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)-ethyl]thien-2-ylsulfonyl}glycine ethyl ester as a white solid. 1H NMR (300 MHz, DMSO-d6, δ1.10 (t, J=7 Hz, 3H), 1.17 (s, 9H), 1.62 (m, 3H), 1.90 (m, 1H), 2.52 (m, 1H), 2.91 (m, 3H), 3.25 (m, 1H), 3.68 (d, J=4.9 Hz, 2H), 3.97 (q, J=7 Hz, 2H), 6.45 (s, 1H), 6.92 (d, J=3.5 Hz, 1H, 7.38 (d, J=3.5 Hz, 1H), 8.31 (t, J=4.9 Hz, 1H).

Workup

  1. waitThe hydrogenation was resumed for another 24 hours
  2. filtrationthe reaction mixture was then filtered through Celite®
  3. concentrationthe filtrate concentrated in vacuo
  4. customchromatographed on silica gel using 3.5% CH3OH and chloroform

Sources & evidence

ORD record
ord-7fb694af80984dac9d9e0cb234dd4a7d
Source dataset
uspto-grants-1998_07
Patent number
US05786358

Reaction notes

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