Methyl trans-2-(3-bromo-2-oxopropyl)-3-methoxypiperidine-1-carboxylate → Methyl trans-2-[3-(3,4-dihydro-4-oxobenzofuro[3,2-d]pyrimidin-3-yl)-2-oxopropyl]-3-methoxy-1-piperidinecarboxylate

HRID 4274Notes

Reaction equation

HRID 4274 reaction equation
[N:1]1[C:6]2[C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[O:9][C:5]=2[C:4](=[O:14])[NH:3][CH:2]=1.[CH3:15][O:16][C@@H:17]1[CH2:22][CH2:21][CH2:20][N:19]([C:23]([O:25][CH3:26])=[O:24])[C@H:18]1[CH2:27][C:28](=[O:31])[CH2:29]Br>>[O:14]=[C:4]1[N:3]([CH2:29][C:28](=[O:31])[CH2:27][C@H:18]2[C@H:17]([O:16][CH3:15])[CH2:22][CH2:21][CH2:20][N:19]2[C:23]([O:25][CH3:26])=[O:24])[CH:2]=[N:1][C:6]2[C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[O:9][C:5]1=2

Participants

3

Reactant 2

HCID 86741990Methyl trans-2-(3-bromo-2-oxopropyl)-3-methoxypiperidine-1-carboxylateHCID 1354154698-Oxa-3,5-diazatricyclo[7.4.0.0,2,7]trideca-1(13),2(7),3,9,11-pentaen-6-one

Product 1

HCID 70393670Methyl trans-2-[3-(3,4-dihydro-4-oxobenzofuro[3,2-d]pyrimidin-3-yl)-2-oxopropyl]-3-methoxy-1-piperidinecarboxylate

Procedure

According to the method of Example 1, 1.22 g (0.0066 mole) of benzofuro[3,2-d]pyrimidin-4(3H)-one [S. S. Sangapure and Y. S. Agasimundin, Indian J. Chem., 14B, 688-691 (1976)] and 0.0066 moles of methyl trans-3-methoxy-2-(3-bromo-2-oxopropyl)-1-piperidinecarboxylate were combined to give the title compound: yield 0.627 g (23%); 1H-nmr (CDCl3) delta 1.2-2.1 ppm (multiplet, 4H, CH3OCHCH2CH2CH2N), 2.7-3.2 (multiplet, 2H, NCH2), 2.9 (doublet, 2H, COCH2CH), 3.3 (singlet, 3H, CHOCH3), 3.7 (singlet, 3H, CO2CH3), 4.0 (broad doublet, 1H CHOCH3), 4.9 (broad triplet, 1H, CH2CHNCO), 5.2 (singlet, 2H, NCH2CO), 7.3-7.7 (multiplet, 3H, aromatic H), 8.0 (doublet, 1H, aromatic H), 8.2 (singlet, 1H, N=CH--N).

Sources & evidence

ORD record
ord-0dbed953e7ea41bf9d9c0da06739cec1
Source dataset
uspto-grants-1988_02
Patent number
US04725599

Reaction notes

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