Formaldehyde → HCID 67261567, compound

HRID 79345Notes

Reaction equation

HRID 79345 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][C@@H:33]3[C@@H:37]([OH:38])[CH2:36][CH2:35][NH:34]3)[N:26]=2)[N:4]=1)[CH3:2].C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:43](C)=O.[Na+]>CO>[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][C@@H:33]3[C@@H:37]([OH:38])[CH2:36][CH2:35][N:34]3[CH3:43])[N:26]=2)[N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67260811HCID 67260811, compound

Product 1

HCID 67261567HCID 67261567, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To N-(3-ethyl-1-((6-(((2R,3S)-3-hydroxypyrrolidin-2-yl)methoxy)pyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (5 mg, 0.0098 mmol; prepared as in Example 36) in MeOH (1 mL) was added HCHO as a 35% aqueous solution (16 mg, 0.20 mmol) and NaBH(OAc)3 (10 mg, 0.049 mmol). The reaction mixture was stirred for 30 minutes, concentrated under reduced pressure and purified by silica gel chromatography (DCM/MeOH/NH4OH 10:1:0.1) to provide the final product (4 mg). MS (ES+APCI) m/z=526 (M+H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by silica gel chromatography (DCM/MeOH/NH4OH 10:1:0.1)

Sources & evidence

ORD record
ord-2c7faf0d20554584a4e7f629fc45cf6f
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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