Hydrochloric Acid → HCID 66820243, compound

HRID 241221Notes

Reaction equation

HRID 241221 reaction equation
CC([CH:5]1[CH2:11][N:10](C([O-])=O)[CH2:9][C:8]2[CH:15]=[C:16]([C:19]3[CH:20]=[C:21]4[NH:27][C:26]([NH:28][C:29]([O:31]CC5C=CC=CC=5)=[O:30])=[N:25][C:22]4=[N:23][CH:24]=3)[CH:17]=[CH:18][C:7]=2[O:6]1)(C)C.[ClH:39]>CO.O1CCOCC1>[ClH:39].[C:8]1([CH2:9][N:28]([C:26]2[NH:27][C:21]3[C:22]([N:25]=2)=[N:23][CH:24]=[C:19]([C:16]2[CH:17]=[CH:18][C:7]4[O:6][CH2:5][CH2:11][NH:10][CH2:9][C:8]=4[CH:15]=2)[CH:20]=3)[C:29](=[O:30])[OH:31])[CH:15]=[CH:16][CH:17]=[CH:18][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86647858HCID 86647858, compound

Product 1

HCID 66820243HCID 66820243, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
55 °C

Procedure

To the solution of 1,1-dimethylethyl-7-[2-({[(phenylmethyl)oxy]carbonyl}amino)-1H-imidazo[4,5-b]pyridine-6-yl]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (4.5 g, 8.73 mmol) in methanol (20 ml) was added 4 N HCl in dioxane at room temperature. Then the reaction mixture was heated to 55° C. for 3 hours. After cooling to room temperature, the precipitate collected by filtration, washed with a minimum of methanol and dried to give phenylmethyl[6-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-imidazo[4,5-b]pyridin-2-yl]carbamate hydrochloride (3.0 g, 76% yield). 1HNMR (400 MHz, CD3OD): 8.59 (m, 1H), 8.51 (s, 1H), 7.85 (m, 1H), 7.79-7.75 (m, 1H), 5.37 (s, 2H), 4.53 (s, 2H), 4.37-4.32 (m, 2H), 3.67-3.64 (m, 2H).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe precipitate collected by filtration
  3. washwashed with a minimum of methanol
  4. customdried

Sources & evidence

ORD record
ord-3fee4eb9a2514fccb85d07b69617f4c6
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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