Formaldehyde → HCID 67261658, compound

HRID 79346Notes

Reaction equation

HRID 79346 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]([O:24][CH2:25][C@@H:26]4[C@@H:30]([OH:31])[CH2:29][CH2:28][NH:27]4)=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[N:34]=2)[N:4]=1)[CH3:2].C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:44](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][C:22]([O:24][CH2:25][C@@H:26]4[C@@H:30]([OH:31])[CH2:29][CH2:28][N:27]4[CH3:44])=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[N:34]=2)[N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 70815014N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(((2R,3S)-3-hydroxypyrrolidin-2-yl)methoxy)imidazo[1,2-a]pyridine-3-carboxamide

Product 1

HCID 67261658HCID 67261658, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(((2R,3S)-3-hydroxypyrrolidin-2-yl)methoxy)imidazo[1,2-a]pyridine-3-carboxamide (5 mg, 0.0095 mmol; Example 38 in MeOH (1 mL) was added HCHO (as a 35% aqueous solution) (7.7 mg, 0.095 mmol) and NaBH(OAc)3 (10 mg, 0.048 mmol). The reaction mixture was stirred for 30 minutes and concentrated under reduced pressure. Purification by silica gel chromatography (DCM/MeOH/NH4OH 10:1:0.1) provided the final product (3 mg). MS (ES+APCI) m/z=540 (M+H).

Workup

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

Sources & evidence

ORD record
ord-614b49830c49468a8459ce6bf7de9b3e
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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