Hydrochloric Acid → methyl [6-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-imidazo[4,5-b]pyridin-2-yl]carbamate hydrochloride

HRID 241235Notes

Reaction equation

HRID 241235 reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6]1[NH:32][C:9]2=[N:10][CH:11]=[C:12]([C:14]3[CH:15]=[CH:16][C:17]4[O:23][CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][C:18]=4[CH:31]=3)[CH:13]=[C:8]2[N:7]=1)=[O:4].C(#N)C.[ClH:36]>O1CCOCC1>[ClH:36].[O:23]1[C:17]2[CH:16]=[CH:15][C:14]([C:12]3[CH:13]=[C:8]4[NH:7][C:6]([NH:5][C:3](=[O:4])[O:2][CH3:1])=[N:32][C:9]4=[N:10][CH:11]=3)=[CH:31][C:18]=2[CH2:19][NH:20][CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 178502015HCID 178502015, compound

Product 1

HCID 86647862methyl [6-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-imidazo[4,5-b]pyridin-2-yl]carbamate hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 1,1-dimethylethyl 7-(2-{[(methyloxy)carbonyl]amino}-3H-imidazo[4,5-b]pyridin-6-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (0.52 g, 1.2 mmol) was taken into acetonitrile (5 mL) followed by addition of 4M hydrogen chloride in 1,4-dioxane (5 mL) and the mixture was stirred at room temperature for 10 minutes. The reaction mixture was concentrated to give a white solid. It was washed with ether then dried to give methyl [6-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-imidazo[4,5-b]pyridin-2-yl]carbamate hydrochloride salt (0.40 g, 100% yield), MS (EI) for C17H17N5O3: 340 (MH+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto give a white solid
  3. washIt was washed with ether
  4. customthen dried

Sources & evidence

ORD record
ord-01f383768d6146d782e2b7a0b162eb6a
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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