Formaldehyde → Dichloromethane methanol ammonium hydroxide

HRID 79334Notes

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][C@H:25]4[C@H:29]([OH:30])[CH2:28][NH:27][CH2:26]4)=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([CH3:38])[N:33]=2)[N:4]=1)[CH3:2].[BH-](OC(C)=O)(OC(C)=O)[O:40][C:41](C)=O.[Na+].C=O.CO.[CH2:57]([Cl:59])[Cl:58]>>[CH2:57]([Cl:59])[Cl:58].[CH3:13][OH:14].[NH4+:4].[OH-:40].[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][C@H:25]4[C@H:29]([OH:30])[CH2:28][N:27]([CH3:41])[CH2:26]4)=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([CH3:38])[N:33]=2)[N:4]=1)[CH3:2]

Participants

Reactant 4

HCID 712Formaldehyde

HCID 5049666Sodium triacetoxyborohydride

HCID 21226129Dichloromethane methanol

HCID 67260126N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-((3R,4R)-4-hydroxypyrrolidin-3-yloxy)imidazo[1,2-a]pyridine-3-carboxamide

Product 2

HCID 21896990Dichloromethane methanol ammonium hydroxide

HCID 67260694HCID 67260694, compound

Procedure

To N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-((3R,4R)-4-hydroxypyrrolidin-3-yloxy)imidazo[1,2-a]pyridine-3-carboxamide (11 mg, 0.022 mmol; prepared as in Example 33) in MeOH/DCM (1 mL/0.5 mL) was added NaBH(OAc)3 (23 mg, 0.11 mmol) and HCHO (as a 35% aqueous solution) (6.5 mg, 0.22 mmol). The reaction mixture was stirred for 30 minutes and then concentrated under reduced pressure. Silica gel chromatography (DCM/MeOH/NH4OH 10:1:0.1) provided the desired product (3 mg). MS (ES+APCI) m/z=526 (M+H).

Workup

concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-be423d46aac84bed993dd82512015e56
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841455B2

Reaction notes

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