Ethyl 3-chloro-3-oxopropionate → HCID 69479908, compound

HRID 2364453Notes

Reaction equation

HRID 2364453 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:10]=[C:11]([NH:20][CH2:21][CH2:22][CH2:23][N:24]([CH3:35])[C:25]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])[C:12]([C:15](OCC)=[O:16])=[N:13][CH:14]=2)=[CH:4][CH:3]=1.Cl[C:37](=[O:44])[CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:10]=[C:11]3[C:12]([C:15]([OH:16])=[C:38]([C:39]([O:41][CH2:42][CH3:43])=[O:40])[C:37](=[O:44])[N:20]3[CH2:21][CH2:22][CH2:23][N:24]([CH3:35])[C:25]([O:27][CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[O:26])=[N:13][CH:14]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 118931Ethyl 3-chloro-3-oxopropionateHCID 69482270HCID 69482270, compound

Product 1

HCID 69479908HCID 69479908, compound

Procedure

This compound was prepared in two steps from ethyl 5-[(4-fluorophenyl)methyl]-3-{[3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)propyl]amino}-2-pyridinecarboxylate and ethyl 3-chloro-3-oxopropionate employing methods similar to those described in Example 457, Steps 3-4. The product was obtained as a white solid: 1H NMR (d6-DMSO, 80° C.) δ 8.65 (1H, b), 7.73 (1H, b), 7.23-7.39 (7H, m), 7.10 (2H, t, J=7 Hz), 5.05 (2H, s), 3.90-4.12 (4H, m), 3.40 (2H, q, J=7 Hz), 3.32 (2H, b), 2.85 (3H, s), 1.74 (2H, b), 1.09 (3H, t, J=7 Hz); ES+ MS: 470 (M+Na+).

Workup

  1. customThe product was obtained as a white solid

Sources & evidence

ORD record
ord-e9f4779901234e69a9dacb077cd538ae
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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