1,1-dimethylethyl 7-(2-methyl-1-{[(2-methylpropyl)-oxy]carbonyl}-1H-imidazo[4,5-b]pyridine-6-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)carboxylate → 2-methylpropyl 2-methyl-6-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-imidazo[4,5-b]pyridine-1-carboxylate

HRID 241149Notes

Reaction equation

HRID 241149 reaction equation
[CH3:1][C:2]1[N:3]([C:29]([O:31][CH2:32][CH:33]([CH3:35])[CH3:34])=[O:30])[C:4]2[C:5]([N:28]=1)=[N:6][CH:7]=[C:8]([C:10]1[CH:11]=[CH:12][C:13]3[O:19][CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][C:14]=3[CH:27]=1)[CH:9]=2>CO.Cl.O1CCOCC1>[CH3:1][C:2]1[N:3]([C:29]([O:31][CH2:32][CH:33]([CH3:35])[CH3:34])=[O:30])[C:4]2[C:5]([N:28]=1)=[N:6][CH:7]=[C:8]([C:10]1[CH:11]=[CH:12][C:13]3[O:19][CH2:18][CH2:17][NH:16][CH2:15][C:14]=3[CH:27]=1)[CH:9]=2

Participants

5

Reactant 1

HCID 668201401,1-dimethylethyl 7-(2-methyl-1-{[(2-methylpropyl)-oxy]carbonyl}-1H-imidazo[4,5-b]pyridine-6-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)carboxylate

Product 1

HCID 668204282-methylpropyl 2-methyl-6-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-imidazo[4,5-b]pyridine-1-carboxylateYield 105.1%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1,1-dimethylethyl 7-(2-methyl-1-{[(2-methylpropyl)-oxy]carbonyl}-1H-imidazo[4,5-b]pyridine-6-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)carboxylate (1.1 g, 2.3 mmol) in methanol (6 ml) and 4 N hydrochloric acid in dioxane (12 ml) was stirred at room temperature for 1 h and then concentrated. The resulting solid was triturated with ethyl acetate to afford the hydrochloride salt of 2-methylpropyl 2-methyl-6-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-imidazo[4,5-b]pyridine-1-carboxylate (0.92 g, 91% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6): 9.78 (s, 1H), 8.79 (d, 1H), 8.42 (d, 1H), 7.88 (d, 1H), 7.70 (dd, 1H), 7.24 (d, 1H), 4.42 (brs, 2H), 4.32 (d, 2H), 4.27 (brs, 2H), 3.50 (brs, 2H), 2.82 (s, 3H), 2.19 (m, 1H), 1.06 (d, 6H); MS (EI) for C21H24N4O3: 381 (MH+).

Workup

  1. concentrationconcentrated
  2. customThe resulting solid was triturated with ethyl acetate

Sources & evidence

ORD record
ord-58773d80ddde4437883efc3d41418135
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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