Ethanol → HCID 178518912, compound

HRID 1620402Notes

Reaction equation

HRID 1620402 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:17]=[CH:16]C(C#N)=[C:12]([CH:18]=O)[N:11]=1.[NH2:20][NH2:21].[CH3:22][CH2:23][OH:24]>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:17]=[CH:16][C:22]2[C:12]([N:11]=1)=[CH:18][N:21]=[N:20][C:23]=2[OH:24]

Participants

4

Reactant 3

HCID 702EthanolHCID 9321HydrazineHCID 84819808HCID 84819808, compound

Product 1

HCID 178518912HCID 178518912, compound

Procedure

To the product of step 3 in 3.0 mL of EtOH at 0° C. was added anhydrous hydrazine (0.16 mL, 5.1 mol). The ice bath was removed, and the homogeneous solution was stirred at RT for 15 min, then the EtOH was removed by rotovap. To the remaining mixture at RT was added 2.0 mL of glacial acetic acid, and the mixture stirred at RT for 5 min, then in an oil bath at 95° C. for 10 min. It was cooled to RT, and treated with 3 mL of water. The precipitated yellow solid was filtered, rinsed with 2×1 mL of water followed by 2×1 mL of ether. The solid was dried in a vacuum oven at 45° C. for 18 h, to afford 2-(2,4-difluorophenylamino)pyrido[3,2-d]pyridazin-5-ol as a yellow crystalline solid. MS (ESI, pos.ion) m/z: M+1=275.1

Workup

  1. customThe ice bath was removed
  2. customthe EtOH was removed by rotovap
  3. additionTo the remaining mixture at RT was added 2.0 mL of glacial acetic acid
  4. stirringthe mixture stirred at RT for 5 min
  5. waitin an oil bath at 95° C. for 10 min
  6. temperatureIt was cooled to RT
  7. additiontreated with 3 mL of water
  8. filtrationThe precipitated yellow solid was filtered
  9. washrinsed with 2×1 mL of water
  10. customThe solid was dried in a vacuum oven at 45° C. for 18 h

Sources & evidence

ORD record
ord-c91bbe1071ad49ddb537d52983f4095f
Source dataset
uspto-grants-2014_07
Patent number
US08772481B2

Reaction notes

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