Hydrochloric Acid → Tetrahydro-pyran-4-carboxylic acid [7-aminomethyl-6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridin-3-yl]-amide

HRID 420535Notes

Reaction equation

HRID 420535 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])=[CH:13][N:12]2[C:23]([NH:26][C:27]([CH:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[O:28])=[CH:24][N:25]=[C:11]2[CH:10]=1)(C)(C)C.Cl>O1CCOCC1>[NH2:7][CH2:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])=[CH:13][N:12]2[C:23]([NH:26][C:27]([CH:29]3[CH2:30][CH2:31][O:32][CH2:33][CH2:34]3)=[O:28])=[CH:24][N:25]=[C:11]2[CH:10]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57906481{6-(2,4-Dichloro-phenyl)-3-[(tetrahydro-pyran-4-carbonyl)-amino]-imidazo[1,2-a]pyridin-7-ylmethyl}-carbamic acid tert-butyl ester

Product 1

HCID 57906482Tetrahydro-pyran-4-carboxylic acid [7-aminomethyl-6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridin-3-yl]-amideYield 77.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of {6-(2,4-dichloro-phenyl)-3-[(tetrahydro-pyran-4-carbonyl)-amino]-imidazo[1,2-a]pyridin-7-ylmethyl}-carbamic acid tert-butyl ester (79.5 mg, 0.153 mmol) in dioxane (3 mL) was added a 4M HCl solution in dioxane (2 mL) and the mixture was stirred at RT for 15 min. The formed precipitate was filtered and dried under vacuum to yield the title compound (2HCl salt, 58 mg, 0.118 mmol, 48%) as a brownish solid. MS: 419 [M+1]+; HPLC: AtRet=0.83.

Workup

  1. filtrationThe formed precipitate was filtered
  2. customdried under vacuum

Sources & evidence

ORD record
ord-24070c377f5b4c25bbe34459ed13d069
Source dataset
uspto-grants-2012_01
Patent number
US08097617B2

Reaction notes

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