Acetic Acid → 7-(4-Bromo-2-chlorophenylamino)-8-chloro-3-methylaminomethylimidazo[1,2-a]pyridine-6-carboxylic acid methyl ester

HRID 857516Notes

Reaction equation

HRID 857516 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][C:19]=2[Cl:25])=[C:7]([Cl:16])[C:8]2[N:9]([C:11]([CH:14]=O)=[CH:12][N:13]=2)[CH:10]=1)=[O:4].C(O)(=O)C.[CH3:30][NH2:31].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH3:1][O:2][C:3]([C:5]1[C:6]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][C:19]=2[Cl:25])=[C:7]([Cl:16])[C:8]2[N:9]([C:11]([CH2:14][NH:31][CH3:30])=[CH:12][N:13]=2)[CH:10]=1)=[O:4]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 6329MethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 865967817-(4-Bromo-2-chlorophenylamino)-8-chloro-3-formyl-imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester

Product 1

HCID 688627777-(4-Bromo-2-chlorophenylamino)-8-chloro-3-methylaminomethylimidazo[1,2-a]pyridine-6-carboxylic acid methyl esterYield 46.8%

Procedure

A suspension of 7-(4-bromo-2-chlorophenylamino)-8-chloro-3-formylimidazo[1,2-a]pyridine-6-carboxylic acid methyl ester (58) (25 mg, 0.056 mmol), acetic acid (7 μL, 0.11 mmol), and methylamine (2.0 M solution in THF, 56 μL, 0.11 mmol) was stirred for 0.5 hours. Sodium triacetoxyborohydride (36 mg, 0.17 mmol) was added and the solution allowed to stir overnight. The reaction mixture was concentrated to dryness and flashed (dichloromethane followed by 10:1 dichloromethane/methanol) to provide the desired product as a yellow solid (12 mg, 46%). MS (APCI+) m/z 455, 457, 459 (M+; Cl, Br pattern) detected.

Workup

  1. stirringto stir overnight
  2. concentrationThe reaction mixture was concentrated to dryness

Sources & evidence

ORD record
ord-1f5c20711a934e44856ff59e99a326e7
Source dataset
uspto-grants-2006_12
Patent number
US07144907B2

Reaction notes

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