Acetic Acid → HCID 57917469, compound

HRID 69251Notes

Reaction equation

HRID 69251 reaction equation
[Cl:1][C:2]1[C:11]([CH:12]([C:14]2[N:18]3[N:19]=[C:20]([C:23]4[CH:24]=[N:25][N:26]([CH:28]5[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]5)[CH:27]=4)[CH:21]=[CH:22][C:17]3=[N:16][CH:15]=2)[CH3:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C=O.[C:36]([BH3-])#N.[Na+].C(O)(=O)C>CO>[Cl:1][C:2]1[C:11]([CH:12]([C:14]2[N:18]3[N:19]=[C:20]([C:23]4[CH:24]=[N:25][N:26]([CH:28]5[CH2:29][CH2:30][N:31]([CH3:36])[CH2:32][CH2:33]5)[CH:27]=4)[CH:21]=[CH:22][C:17]3=[N:16][CH:15]=2)[CH3:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 57917287(Rac)-5-chloro-6-{1-[6-(1-piperidin-4-yl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-ethyl}-quinoline

Product 1

HCID 57917469HCID 57917469, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To (rac)-5-chloro-6-{1-[6-(1-piperidin-4-yl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-ethyl}-quinoline (131 mg, 0.287 mmol), a 37% aqueous solution of formaldehyde (0.107 mL, 1.434 mmol) and 85% sodium cyanoborohydride (106 mg, 1.434 mmol) in MeOH (5 mL) was added acetic acid to adjust pH at 5-6. The RM was stirred at rt for 2.5 h, filtered and purified by preparative HPLC with acetonitrile and water (+0.1% TFA) to yield the title compound as a white foam (tR 2.29 min (conditions 8), MH+=472).

Workup

  1. filtrationfiltered
  2. custompurified by preparative HPLC with acetonitrile and water (+0.1% TFA)

Sources & evidence

ORD record
ord-b51b1ec7c9e34cc7a8688a5088065c90
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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