Dichloromethane → Dichloromethane methanol ammonium hydroxide

HRID 79329

Reaction equation

HRID 79329 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]([CH2:24][N:25]4[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]4)=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([CH3:45])[N:40]=2)[N:4]=1)[CH3:2].C(O)(C(F)(F)F)=[O:47].[CH2:53]([Cl:55])[Cl:54]>>[CH2:53]([Cl:55])[Cl:54].[CH3:13][OH:14].[NH4+:4].[OH-:47].[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]([CH2:24][N:25]4[CH2:26][CH2:27][NH:28][CH2:29][CH2:30]4)=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([CH3:45])[N:40]=2)[N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 70814959tert-butyl 4-((3-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-ylcarbamoyl)imidazo[1,2-a]pyridin-7-yl)methyl)piperazine-1-carboxylate

Product 2

HCID 21896990Dichloromethane methanol ammonium hydroxideHCID 67260131N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(piperazin-1-ylmethyl)imidazo[1,2-a]pyridine-3-carboxamide

Procedure

To tert-butyl 4-((3-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-ylcarbamoyl)imidazo[1,2-a]pyridin-7-yl)methyl)piperazine-1-carboxylate (11 mg, 0.018 mmol) in DCM (1 mL) was added TFA (1 mL). 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 final product (6 mg). MS (ES+APCI) m/z=509 (M+H).

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5df34623653440cc908d46d42259e0e9
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Linked notes

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