Ammonia → HCID 54767995, compound

HRID 1503279Notes

Reaction equation

HRID 1503279 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[CH:5]([NH2:29])[CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:18][CH:17]=3)[CH:14]=2)[NH:9][CH:8]=1)[CH3:2].[NH3:31]>CCOC(C)=O>[CH3:2][CH2:1][O:3][C:4]([CH3:5])=[O:30].[CH3:1][OH:3].[NH4+:9].[OH-:3].[NH2:29][CH:5]([CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]3[CH:17]=[CH:18][C:19]([O:22][C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[CH:20][CH:21]=3)[CH:14]=2)[NH:9][CH:8]=1)[C:4]([NH2:31])=[O:3]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 54767996HCID 54767996, compound

Product 2

HCID 21901312Ethyl acetate methanol ammonium hydroxideHCID 54767995HCID 54767995, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

2-Amino-3-[5-(4-phenoxyphenyl)-1H-indol-3-yl]propionamide (8) was prepared as follows. A mixture of compound 7 prepared in Example 1 (0.2 g), NH3 (7N in MeOH, 6 mL) was shaken at 70° C. for 36 hours. EtOAc (40 mL) was added to the reaction mixture, then, washed with water and brine, concentrated and purified by column (EtOAc/MeOH 10/1, then EtOAc/MeOH/NH4OH 10/2/0.5) to afford compound 8 as a yellow solid (0.11 g, 64%): 1H-NMR (400 MHz, CD3OD) δ: 7.85 (s, 1H), 7.68-7.72 (m, 2H), 7.35-7.41 (m, 4H), 7.02-7.15 (m, 5H), 3.74-3.78 (m, 1H), 3.25-3.3 (m, 1H), 3.04-3.14 (m, 1H); LC/MS: m/z=372.5 [M+H]+ (Calc: 371.4).

Workup

  1. custom2-Amino-3-[5-(4-phenoxyphenyl)-1H-indol-3-yl]propionamide (8) was prepared
  2. washwashed with water and brine
  3. concentrationconcentrated
  4. custompurified by column (EtOAc/MeOH 10/1

Sources & evidence

ORD record
ord-cc3353437b364da2be9ae0198f246a93
Source dataset
uspto-grants-2015_12
Patent number
US09212139B2

Reaction notes

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