Ammonia → HCID 54767999, compound

HRID 1503282Notes

Reaction equation

HRID 1503282 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][C:12]([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:13][CH:14]=2)[NH:9][CH:8]=1)[CH3:2].[NH3:31].C[CH2:33][O:34]C(C)=O>O>[CH3:2][CH2:1][O:3][C:4]([CH3:5])=[O:30].[CH3:33][OH:34].[NH4+:9].[OH-:3].[NH2:29][CH:5]([CH2:6][C:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[CH:18][CH:17]=3)=[CH:13][CH:14]=2)[NH:9][CH:8]=1)[C:4]([NH2:31])=[O:3]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 54765770HCID 54765770, compound

Product 2

HCID 21901312Ethyl acetate methanol ammonium hydroxideHCID 54767999HCID 54767999, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

2-Amino-3-[6-(4-phenoxyphenyl)-1H-indol-3-yl]propionamide (15) was prepared as follows: A mixture of compound 14 prepared in Example 4 (0.2 g) and NH3 (7N in MeOH, 6 mL, and 28% aqueous, 2 mL) was shaken at 70° C. for 16 hours. EtOAc (40 mL) and water (10 mL) were added to the reaction mixture. The organic layer was separated, concentrated and purified by column (EtOAc/MeOH 10/1, then EtOAc/MeOH/NH4OH 10/2/0.5) to afford compound 15 as a brown solid (0.1 g, 53%): 1H-NMR (400 MHz, CD3OD) δ: 7.6 (d, 1H, 8.3 Hz), 7.46-7.55 (m, 3H), 7.18-7.28 (m, 3H), 7.06 (s, 1H), 6.92-7.05 (m, 5H), 3.58-3.62 (m, 1H), 3.1-3.15 (m, 1H), 2.88-2.94 (m, 1H); LC/MS: m/z=372.1 [M+H]+ (Calc: 371.4).

Workup

  1. custom2-Amino-3-[6-(4-phenoxyphenyl)-1H-indol-3-yl]propionamide (15) was prepared
  2. customThe organic layer was separated
  3. concentrationconcentrated
  4. custompurified by column (EtOAc/MeOH 10/1

Sources & evidence

ORD record
ord-6bb838b9fa104f8598eaa5149bdd099e
Source dataset
uspto-grants-2015_12
Patent number
US09212139B2

Reaction notes

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