Methyl malonyl chloride → HCID 54729995, compound

HRID 2364137Notes

Reaction equation

HRID 2364137 reaction equation
[NH2:1][C:2]1[C:3]([C:15]([O:17]CC)=O)=[N:4][CH:5]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=1.Cl[C:21](=[O:27])[CH2:22][C:23]([O:25][CH3:26])=[O:24]>>[CH2:8]([C:6]1[CH:7]=[C:2]2[C:3]([C:15]([OH:17])=[C:22]([C:23]([O:25][CH3:26])=[O:24])[C:21](=[O:27])[NH:1]2)=[N:4][CH:5]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 123460Methyl malonyl chlorideHCID 42637771HCID 42637771, compound

Product 1

HCID 54729995HCID 54729995, compound

Procedure

This compound was prepared from ethyl 3-amino-5-benzylpyridine-2-carboxylate and methyl 3-chloro-3-oxopropionate employing methods similar to those described in Example 1, Steps 10-11. The product was obtained as a tan solid: 1H NMR (d6-DMSO) δ 11.9 (1H, br), 11.59 (1H, s), 8.46 (1H, d, J=1.6 Hz), 7.43 (1H, d, J=1.6 Hz), 7.33-7.20 (5H, m), 4.11 (2H, s), 3.74 (3H, s); HRMS calcd for C17H14N2O4+H+: 311.1032. Found: 311.1025.

Workup

  1. customThe product was obtained as a tan solid

Sources & evidence

ORD record
ord-356a61824abd4d868919c1599010c01e
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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