Formaldehyde → 2-(4-(1-((3-(Hydroxymethyl)imidazo[1,2-a]pyridin-6-yl)methyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)-1H-pyrazol-1-yl)ethanol

HRID 876860Notes

Reaction equation

HRID 876860 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH2:10][N:11]2[C:15]3=[N:16][C:17]([C:20]4[CH:21]=[N:22][N:23](C)[CH:24]=4)=[CH:18][N:19]=[C:14]3[N:13]=[N:12]2)=[CH:2]1.[C:26]([O-])(=O)[CH3:27].[Na+].[CH2:31]=[O:32].[OH-:33].[Na+]>C(O)(=O)C>[OH:32][CH2:31][C:8]1[N:1]2[CH:2]=[C:3]([CH2:10][N:11]3[C:15]4=[N:16][C:17]([C:20]5[CH:24]=[N:23][N:22]([CH2:26][CH2:27][OH:33])[CH:21]=5)=[CH:18][N:19]=[C:14]4[N:13]=[N:12]3)[CH:9]=[CH:4][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 673059931-((1H-Pyrrolo[2,3-b]pyridin-3-yl)methyl)-6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]-triazolo[4,5-b]pyrazine

Product 1

HCID 673061182-(4-(1-((3-(Hydroxymethyl)imidazo[1,2-a]pyridin-6-yl)methyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)-1H-pyrazol-1-yl)ethanol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 306-a (60 mg, 0.13 mmol) (prepared according to the procedure of Compound 1) in 0.1 mL of acetic acid were added sodium acetate (39 mg, 0.48 mmol) and then formaldehyde (0.13 mL, 37% in water). The mixture was stirred at 100° C. overnight. After cooled, the mixture was adjusted to pH>7 with aqueous NaOH. The resulting precipitate was collected and purified by chromatography to afford the title compound (10 mg). MS (m/z): 392.0 (M+H)+

Workup

  1. temperatureAfter cooled
  2. customThe resulting precipitate was collected
  3. custompurified by chromatography

Sources & evidence

ORD record
ord-3b360b11de2247fda03242f9fed19b93
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

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