Water → 4-Chloro-3-cyano-5-hydroxymethyl-pyrrolo[1,2-b]pyridazine-6-carboxylic Acid Ethyl Ester

HRID 2183480Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH2:18]Br)=[C:8]2[C:13]([Cl:14])=[C:12]([C:15]#[N:16])[CH:11]=[N:10][N:9]2[CH:17]=1)=[O:5])[CH3:2].O.C([O-])(O)=[O:22].[Na+]>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH2:18][OH:22])=[C:8]2[C:13]([Cl:14])=[C:12]([C:15]#[N:16])[CH:11]=[N:10][N:9]2[CH:17]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of compound 16A (102 mg, 0.30 mmol) in THF (12 mL) was added water (3 mL) dropwise. The reaction was kept at room temperature for 3 days and then heated to 50° C. for 3 hours. Upon cooling to room temperature, NaHCO3 (70 mg) was added to the reaction mixture. The reaction was concentrated to dryness, redissolved in CH2Cl2 and filtered. The filtrate was concentrated to give compound 16B as a yellow solid (84 mg, 100%). This compound was used in the following steps without further purification.

Workup

temperatureUpon cooling to room temperature
concentrationThe reaction was concentrated to dryness
dissolutionredissolved in CH2Cl2
filtrationfiltered
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-d37f2227c964435d9b1a1e1411f094db
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06900208B2

Reaction notes

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