HCID 178418361, compound → HCID 178423416, compound

HRID 241223Notes

Reaction equation

HRID 241223 reaction equation
C1(COC(=O)[NH:10][C:11]2[NH:41][C:14]3=[N:15][CH:16]=[C:17]([C:19]4[CH:20]=[CH:21][C:22]5[O:28][CH2:27][CH2:26][N:25]([C:29]6[C:38]7[C:33](=[CH:34][CH:35]=[C:36]([CH3:39])[CH:37]=7)[N:32]=[CH:31][N:30]=6)[CH2:24][C:23]=5[CH:40]=4)[CH:18]=[C:13]3[N:12]=2)C=CC=CC=1.[H][H]>C(O)(=O)C.[Pd]>[CH3:39][C:36]1[CH:37]=[C:38]2[C:33](=[CH:34][CH:35]=1)[N:32]=[CH:31][N:30]=[C:29]2[N:25]1[CH2:24][C:23]2[CH:40]=[C:19]([C:17]3[CH:18]=[C:13]4[N:12]=[C:11]([NH2:10])[NH:41][C:14]4=[N:15][CH:16]=3)[CH:20]=[CH:21][C:22]=2[O:28][CH2:27][CH2:26]1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178423415HCID 178423415, compound

Product 1

HCID 178423416HCID 178423416, compoundYield 4.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Phenylmethyl{6-[4-(6-methylquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]-3H-imidazo[4,5-b]pyridin-2-yl}carbamate (0.1 g, 0.18 mmol) in acetic acid (8 ml) was placed under nitrogen. Palladium on carbon (0.25 g, 10 W %) was added and the reaction mixture saturated with hydrogen then stirred at room temperature for 12 h. The reaction mixture was filtered through a pad of celite then concentrated. The residue was taken into a minimum of methanol and purified by preparative reverse phase HPLC to give 6-[4-(6-methylquinazolin-4-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl]-3H-imidazo[4,5-b]pyridin-2-amine (0.0033 g). 1H NMR (400 MHz, d6-DMSO); δ 8.52 (s, 1H), 8.32-8.12 (s, 1H), 7.84-7.47 (m, 6H), 7.07-7.00 (d, 1H), 6.80-6.50 (s, 1H), 5.04 (s, 2H), 4.56-4.44 (m, 2H), 4.20-4.09 (m, 2H), 2.83 (s, 3H); MS (EI) for C24H21N7O: 424.1 (MH+).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationthen concentrated
  3. custompurified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-d3b0392bf10e41faa53acfa80b6afb7b
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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