3-Cyano-5-hydroxymethyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carboxylic Acid Ethyl Ester → 3-Cyano-5-formyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carboxylic Acid Ethyl Ester

HRID 1796601Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH2:31][OH:32])=[C:8]2[C:13]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:17][CH:16]=3)=[C:12]([C:28]#[N:29])[CH:11]=[N:10][N:9]2[CH:30]=1)=[O:5])[CH3:2]>C(Cl)(Cl)Cl.O=[Mn]=O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH:31]=[O:32])=[C:8]2[C:13]([NH:14][C:15]3[CH:16]=[CH:17][C:18]([O:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:19][CH:20]=3)=[C:12]([C:28]#[N:29])[CH:11]=[N:10][N:9]2[CH:30]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of compound 16C (21.4 mg, 0.05 mmol) in chloroform (1 mL) was added MnO2 (<5 micron, activated, 17 mg, 0.20 mmol). The reaction was heated at 55° C. overnight, cooled to room temperature and purified by flash chromatography on a silica gel column (0-2% EtOAc/CH2Cl2) to give compound 18 as a yellow solid (20 mg, 94%). HPLC: 94% at 2.20 min (retention time) (PrimeSphere 5u C18-HC column, 4.6×30 mm eluting with 10-90% MeOH/H2O over 2 minutes containing 0.1% TFA; 5 mL/min, monitoring at 200 nm). MS (ES): m/z 427.0 [M+H]+.

Workup

temperaturecooled to room temperature
custompurified by flash chromatography on a silica gel column (0-2% EtOAc/CH2Cl2)

Sources & evidence

ORD record: ord-f68123ef4e354149a16892c70b85d33b
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030112B2

Reaction notes

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