Water → HCID 19871188, compound

HRID 1906816Notes

Reaction equation

HRID 1906816 reaction equation
CC(N[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH:12]=[CH:13][C:14]3[N:15]([C:17]([CH3:20])=[N:18][N:19]=3)[N:16]=2)[CH:6]=1)C.[CH:21]([N:24](C(C)C)[CH2:25][CH3:26])([CH3:23])[CH3:22].C(Cl)(=[O:32])C.O>ClCCl>[CH3:22][CH:21]([NH:24][C:25](=[O:32])[CH2:26][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH:12]=[CH:13][C:14]3[N:15]([C:17]([CH3:20])=[N:18][N:19]=3)[N:16]=2)[CH:6]=1)[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 15595705HCID 15595705, compound

Product 1

HCID 19871188HCID 19871188, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2 g of N-(1-methylethyl)-3-(3-methyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl)benzenamine and 1.43 ml diisopropylethylamine in 200 ml of dichloromethane was added 0.6 ml of acetylchloride. This solution was stirred for 12 hours, then poured onto 200 ml of water and extracted with 150 ml portions of dichloromethane. The combined extracts were dried, concentrated in vacuo and the solid chromatographed on 300 g of silica gel using dichloromethane-methanol (97:3). The fractions containing the desired product were combined, concentrated in vacuo and the solid recrystalized from dichloromethane-hexane to give 0.72 g of yellow crystals, mp 197°-200° C.

Workup

  1. extractionextracted with 150 ml portions of dichloromethane
  2. customThe combined extracts were dried
  3. concentrationconcentrated in vacuo
  4. customthe solid chromatographed on 300 g of silica gel
  5. additionThe fractions containing the desired product
  6. concentrationconcentrated in vacuo
  7. customthe solid recrystalized from dichloromethane-hexane

Sources & evidence

ORD record
ord-139bd06d2f3a49698949a31ed03a0cd6
Source dataset
uspto-grants-1987_03
Patent number
US04654343

Reaction notes

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