Trifluoroacetic acid → HCID 69675378, compound

HRID 473899Notes

Reaction equation

HRID 473899 reaction equation
[CH3:1][CH:2]([CH3:34])[CH2:3][O:4][C:5]([N:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([C:16]3[CH:17]=[CH:18][C:19]4[O:25][CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][C:20]=4[CH:33]=3)[CH:14]=2)[N:9]=[CH:8]1)=[O:6].FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[O:25]1[C:19]2[CH:18]=[CH:17][C:16]([C:13]3[CH:14]=[C:15]4[N:7]([C:5]([O:4][CH2:3][CH:2]([CH3:34])[CH3:1])=[O:6])[CH:8]=[N:9][C:10]4=[N:11][CH:12]=3)=[CH:33][C:20]=2[CH2:21][NH:22][CH2:23][CH2:24]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 70815046HCID 70815046, compound

Product 1

HCID 69675378HCID 69675378, compoundYield 117.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1,1-dimethylethyl 7-(1-{[(2-methylpropyl)oxy]carbonyl}-1H-imidazo[4,5-b]pyridine-6-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (0.40 g, 0.86 mmol) in chloroform (4 mL) was added dropwise trifluoroacetic acid (5 mL) and the solution then warmed to 80° C. for 45 minutes. After cooling, the solution was concentrated and dried to give 2-methylpropyl 6-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-imidazo[4,5-b]pyridine-1-carboxylate (0.37 g, 90% yield) as the trifluoroacetic acid salt. MS (EI) for C20H25N4O3: 367 (MH+).

Workup

  1. temperatureAfter cooling
  2. concentrationthe solution was concentrated
  3. customdried

Sources & evidence

ORD record
ord-a4f610fcec6542d8bf95e9046de86e70
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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