Triethylamine → 3-[2-(2,4-difluorophenoxy)-6-oxo-6H-pyrido[1,2-b]pyridazin-5-yl]-4-methoxybenzoic propanoic anhydride

HRID 1454959Notes

Reaction equation

HRID 1454959 reaction equation
[F:1][C:2]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH:11]=[CH:12][C:13](=[O:26])[C:14]=2[C:15]2[CH:16]=[C:17]([CH:21]=[CH:22][C:23]=2[O:24][CH3:25])[C:18]([OH:20])=[O:19])[N:10]=1.C(N([CH2:37][CH3:38])CC)C.[CH2:39]([O:41]C(Cl)=O)C>C(Cl)Cl>[C:39]([O:19][C:18](=[O:20])[C:17]1[CH:21]=[CH:22][C:23]([O:24][CH3:25])=[C:15]([C:14]2[C:13](=[O:26])[CH:12]=[CH:11][N:9]3[C:8]=2[CH:7]=[CH:6][C:5]([O:4][C:3]2[CH:27]=[CH:28][C:29]([F:31])=[CH:30][C:2]=2[F:1])=[N:10]3)[CH:16]=1)(=[O:41])[CH2:37][CH3:38]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 575312343-(2-(2,4-Difluorophenoxy)-6-oxo-6H-pyrido[1,2-b]pyridazin-5-yl)-4-methoxybenzoic acid2×

Product 1

HCID 866128473-[2-(2,4-difluorophenoxy)-6-oxo-6H-pyrido[1,2-b]pyridazin-5-yl]-4-methoxybenzoic propanoic anhydride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-[2-(2,4-difluorophenoxy)-6-oxo-6H-pyrido[1,2-b]pyridazin-5-yl]-4-methoxybenzoic acid (Intermediate 1, 424 mg, 1.0 mmol) in CH2Cl2 (10 mL) was added triethyl amine (202 mg, 2.0 mmol) and ethylchloroformate (162 mg, 1.8 mmol) at 0° C. The mixture was warmed to ambient temperature and stirred for 10 min. The reaction was complete by LCMS analysis and concentrated in vacuo to yield 3-[2-(2,4-difluorophenoxy)-6-oxo-6H-pyrido[1,2-b]pyridazin-5-yl]-4-methoxybenzoic propanoic anhydride.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-899dedf5a24b4d11af6efac366e7bb59
Source dataset
uspto-grants-2009_01
Patent number
US07482345B2

Reaction notes

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