HCID 67263692, compound → HCID 67264544, compound

HRID 1040833Notes

Reaction equation

HRID 1040833 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]2[CH2:8][CH2:9][N:10]([CH2:13][C@H:14]([O:19][CH3:20])[C:15]([F:18])([F:17])[F:16])[CH2:11][CH2:12][C:6]=2[CH:5]=1)([O-])=O>CO.[Pd]>[F:18][C:15]([F:16])([F:17])[C@@H:14]([O:19][CH3:20])[CH2:13][N:10]1[CH2:11][CH2:12][C:6]2[CH:5]=[C:4]([NH2:1])[CH:22]=[CH:21][C:7]=2[CH2:8][CH2:9]1

Participants

4

Reactant 1

HCID 67263692HCID 67263692, compound

Product 1

HCID 67264544HCID 67264544, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

7-Nitro-3-((S)-3,3,3-trifluoro-2-methoxy-propyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (171 mg, 0.538 mmol, 1.0 eq) was placed in methanol (20 mL) and 10% palladium on carbon (17 mg) was added. The reaction was hydrogenated at 25 psi for 30 minutes. The mixture was then filtered through celite and concentrated under reduced pressure to obtain 3-((S)-3,3,3-trifluoro-2-methoxy-propyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine as a green amorphous solid (113 mg, 73%). LCMS (m/e) 289 (M+1); 1H-NMR (CDCl3, 400 MHz) δ 6.89 (d, 1H, J=7.5 Hz), 6.51-6.45 (m, 2H), 3.76-3.66 (m, 1H), 3.61 (s, 3H), 3.63-3.52 (m, 2H), 2.88-2.79 (m, 6H), 2.78-2.69 (m, 4H).

Workup

  1. filtrationThe mixture was then filtered through celite and
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e5a511e8fcb1476a99c429f4a5f3b033
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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