Benzyl 4-((1E,4E)-2-amino-4-(dipropylcarbamoyl)-3H-benzo[b]azepin-8-yl)benzoate → HCID 51034286, compound

HRID 593462Notes

Reaction equation

HRID 593462 reaction equation
[NH2:1][C:2]1[CH2:3][C:4]([C:29](=[O:37])[N:30]([CH2:34][CH2:35][CH3:36])[CH2:31][CH2:32][CH3:33])=[CH:5][C:6]2[CH:12]=[CH:11][C:10]([C:13]3[CH:28]=[CH:27][C:16]([C:17]([O:19]CC4C=CC=CC=4)=[O:18])=[CH:15][CH:14]=3)=[CH:9][C:7]=2[N:8]=1.[H][H]>CO.[Pd]>[NH2:1][C:2]1[CH2:3][C:4]([C:29](=[O:37])[N:30]([CH2:34][CH2:35][CH3:36])[CH2:31][CH2:32][CH3:33])=[CH:5][C:6]2[CH:12]=[CH:11][C:10]([C:13]3[CH:28]=[CH:27][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=3)=[CH:9][C:7]=2[N:8]=1

Participants

5

Reactant 2

HCID 67087564Benzyl 4-((1E,4E)-2-amino-4-(dipropylcarbamoyl)-3H-benzo[b]azepin-8-yl)benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 51034286HCID 51034286, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Benzyl 4-((1E,4E)-2-amino-4-(dipropylcarbamoyl)-3H-benzo[b]azepin-8-yl)benzoate (0.025 g, 0.0504 mmol) was suspended in 1 ml of methanol, and 25 mgs of 10% Pd/C (Degussa type) was added and the mixture was hydrogenated under a balloon of hydrogen for one hour. This mixture was then filtered through GF/F filter paper, and the filtrate was concentrated to 16 mgs of 4-((1E,4E)-2-amino-4-(dipropylcarbamoyl)-3H-benzo[b]azepin-8-yl)benzoic acid (78%). 1H NMR (400 MHz, DMSO-d6) δ 7.98-8.03 (m, 2H), 7.76-7.82 (m, 2H), 7.38-7.43 (m, 1H), 7.33-7.37 (m, 1H), 7.27-7.31 (m, 1H), 6.92 (br s, 1H), 6.76 (s, 1H), 3.28-3.36 (m, 4H, partially obscurred by water peak), 2.74 (s, 2H), 1.51-1.62 (m, 4H), 0.71-0.97 (m, 6H); m/z (APCI-pos) M+1=406.2.

Workup

  1. filtrationThis mixture was then filtered through GF/F
  2. filtrationfilter paper
  3. concentrationthe filtrate was concentrated to 16 mgs of 4-((1E,4E)-2-amino-4-(dipropylcarbamoyl)-3H-benzo[b]azepin-8-yl)benzoic acid (78%)

Sources & evidence

ORD record
ord-44adbe0dc5af4a0998533b9de315ff5c
Source dataset
uspto-grants-2016_01
Patent number
US09242964B2

Reaction notes

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