Ethanolamine → HCID 69309187, compound

HRID 2250600Notes

Reaction equation

HRID 2250600 reaction equation
[Cl:1][C:2]1[N:6]2[N:7]=[C:8]([CH:20]([CH3:22])[CH3:21])[C:9]([CH:18]=O)=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:5]2=[CH:4][CH:3]=1.[NH2:23][CH2:24][CH2:25][OH:26].C([BH3-])#N.[Na+]>C(O)C.C(O)(=O)C>[Cl:1][C:2]1[N:6]2[N:7]=[C:8]([CH:20]([CH3:21])[CH3:22])[C:9]([CH2:18][NH:23][CH2:24][CH2:25][OH:26])=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:5]2=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 700EthanolamineHCID 5003444Sodium cyanoborohydride2×HCID 86597470HCID 86597470, compound

Product 1

HCID 69309187HCID 69309187, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalyst2×HCID 702EthanolSolvent

Procedure

To a suspension of 7-chloro-4-(4-fluorophenyl)-2-isopropylpyrrolo[1,2-b]pyridazine-3-carbaldehyde (40 mg) in ethanol (1 mL) was added 2-aminoethanol (11.8 mg), sodium cyanoborohydride (12.1 mg), and acetic acid (1 drop) in an ice-water bath. After 10 minutes, the mixture was stirred at ambient temperature. After 2 hours, sodium cyanoborohydride (11.8 mg) was added and the reaction mixture was acidified to pH4 with acetic acid (5 drops). After stirring overnight, the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated sodium bicarbonate, water, and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by p-TLC (chloroform-methanol=10-1) to give 2-({[7-chloro-4-(4-fluorophenyl)-2-isopropylpyrrolo[1,2-b]pyridazin-3-yl]methyl}amino)ethanol as pale yellow oil (21 mg).

Workup

  1. waitAfter 2 hours
  2. stirringAfter stirring overnight
  3. customthe reaction mixture was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with saturated sodium bicarbonate, water, and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by p-TLC (chloroform-methanol=10-1)

Sources & evidence

ORD record
ord-5a14b7d2604e4463a527382c4075f5d3
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

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