HCID 67515210, compound → HCID 67513726, compound

HRID 473918Notes

Reaction equation

HRID 473918 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:17][CH2:16][CH2:15][N:14]([C:18]([N:20]4[CH:25]5[CH2:26][CH2:27][CH:21]4[CH2:22][C:23]([C:29]([F:32])([F:31])[F:30])([OH:28])[CH2:24]5)=[O:19])[CH2:13][C:12]=3[CH:33]=2)=[CH:4][C:3]=1[N+:34]([O-])=O.[H][H]>[Pd].C(O)(=O)C>[NH2:34][C:3]1[CH:4]=[C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:17][CH2:16][CH2:15][N:14]([C:18]([N:20]4[CH:21]5[CH2:27][CH2:26][CH:25]4[CH2:24][C:23]([C:29]([F:32])([F:31])[F:30])([OH:28])[CH2:22]5)=[O:19])[CH2:13][C:12]=3[CH:33]=2)[CH:6]=[N:7][C:2]=1[NH2:1]

Participants

5

Reactant 2

HCID 67515210HCID 67515210, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67513726HCID 67513726, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A slurry of 8-{[7-(6-amino-5-nitropyridin-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]carbonyl}-3-(trifluoromethyl)-8-azabicyclo[3.2.1]octan-3-ol (1.1 g, 2.2 mmol), Pd/C (5% wt./wt., 0.20 g) and acetic acid (40 mL) was subjected to an atmosphere of hydrogen (45 PSI) using a Parr apparatus. After 2 hours the reaction mixture was filtered through Celite and concentrated to give 8-{[7-(5,6-diaminopyridin-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]carbonyl}-3-(trifluoromethyl)-8-azabicyclo[3.2.1]octan-3-ol (0.95, 92% yield) as an orange oil. MS (ES) for C23H26F3N5O3: 478 (MH+).

Workup

  1. filtrationAfter 2 hours the reaction mixture was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-8d5ada19eb0e4db5b69749014ae05efe
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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