Formic Acid → HCID 66743102, compound

HRID 1431124Notes

Reaction equation

HRID 1431124 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:16]=[CH:15][C:14]([C@@H:17]3[CH2:21][CH2:20][N:19]([C:22](OC(C)(C)C)=O)[CH2:18]3)=[CH:13][CH:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[N:7]=1.C(O)=O.C=O>O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([C@@H:17]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18]3)=[CH:15][N:16]=2)[C:5](=[O:9])[N:6]([CH3:8])[N:7]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 712FormaldehydeHCID 66743342HCID 66743342, compound

Product 1

HCID 66743102HCID 66743102, compoundYield 113.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

(S)-tert-Butyl 3-(6-(6-chloro-2-methyl-3-oxo-2,3-dihydropyridazin-4-ylamino)pyridin-3-yl)pyrrolidine-1-carboxylate (456 mg, 1.12 mmol, Eq: 1.00) was dissolved in a mix of formic acid (20.0 ml) and formaldehyde, 37% (40 ml). The reaction mixture stirred at 70° C. for 18 h. The solution was cooled to room temperature and water was added. The aqueous solution was extracted once with DCM. The aqueous layer was Brought to pH=14 with solid K2CO3. A solid formed and was filtered to give (S)-6-chloro-2-methyl-4-(5-(1-methylpyrrolidin-3-yl)pyridin-2-ylamino)pyridazin-3(2H)-one (408 mg, quantitative yield). LC/MS-ESI observed [M+H]+ 320.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. extractionThe aqueous solution was extracted once with DCM
  3. customA solid formed
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-f8a3a5e86aa849339f289b079d2c13da
Source dataset
uspto-grants-2015_01
Patent number
US08940741B2

Reaction notes

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