Formaldehyde → N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(7-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79383Notes

Reaction equation

HRID 79383 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][C:22]([C:24]4[N:28]5[CH2:29][CH2:30][NH:31][CH2:32][C:27]5=[N:26][CH:25]=4)=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([CH3:40])[N:35]=2)[N:4]=1)[CH3:2].[BH-](OC(C)=O)(OC(C)=O)O[C:43](C)=O.[Na+].C=O>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][C:22]([C:24]4[N:28]5[CH2:29][CH2:30][N:31]([CH3:43])[CH2:32][C:27]5=[N:26][CH:25]=4)=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([CH3:40])[N:35]=2)[N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 53262090N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

Product 1

HCID 67260115N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(7-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-3-yl)imidazo[1,2-a]pyridine-3-carboxamideYield 62.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide (5 mg, 0.0094 mmol; prepared as in Example 59) in MeOH (4 mL) was added NaBH(OAc)3 (8.0 mg, 0.038 mmol), and HCHO (as a 35% aqueous solution) (15 mg, 0.19 mmol). The reaction mixture was stirred for 30 minutes then concentrated under reduced pressure. The residue was purified by silica gel chromatography (DCM/MeOH/NH4OH 10:1:0.1) to provide the final product (3.2 mg). MS (ES+APCI) m/z=546 (M+H).

Workup

  1. concentrationthen concentrated under reduced pressure
  2. customThe residue was purified by silica gel chromatography (DCM/MeOH/NH4OH 10:1:0.1)

Sources & evidence

ORD record
ord-df6b8089a5d84f51a84565066fab7fa0
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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