Trimethylsilyldiazomethane → Ethyl 4-methoxy-6-(4-methoxybenzyl)-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate

HRID 1817342Notes

Reaction equation

HRID 1817342 reaction equation
[OH:1][C:2]1[C:11]2[C:10](=[O:12])[N:9]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[CH2:8][CH2:7][C:6]=2[C:5]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[N:4][CH:3]=1.[Si](C=[N+]=[N-])(C)(C)[CH3:28].FC1C=CC(CN2CCC3C(C(OCC)=O)=NC=C(OC)C=3C2=O)=CC=1>>[CH3:28][O:1][C:2]1[C:11]2[C:10](=[O:12])[N:9]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)[CH2:8][CH2:7][C:6]=2[C:5]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[N:4][CH:3]=1

Participants

4

Reactant 3

HCID 167693TrimethylsilyldiazomethaneHCID 69058090Ethyl 6-(4-fluorobenzyl)-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylateHCID 69058523Ethyl 4-hydroxy-6-(4-methoxybenzyl)-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate

Product 1

HCID 67515740Ethyl 4-methoxy-6-(4-methoxybenzyl)-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate

Procedure

The title product was prepared by treating ethyl 4-hydroxy-6-(4-methoxybenzyl)-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate with TMS-diazomethane, using a method set forth in Step 5 of Example 8 for the preparation of ethyl 6-(4-fluorobenzyl)-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate, except that after quenching with HOAc the reaction was concentrated in vacuo and partitioned between sat aq NaHCO3 and CHCl3. LRMS (M+1)=371.0

Workup

  1. customexcept that after quenching with HOAc the reaction
  2. concentrationwas concentrated in vacuo
  3. custompartitioned

Sources & evidence

ORD record
ord-46a716a0af04497fbbf065404e9dcb03
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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