Ammonium Hydroxide → HCID 21254088, compound

HRID 1531567Notes

Reaction equation

HRID 1531567 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][NH:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])=[CH:27][CH:26]=2)=[CH:15][C:14](C(N2CCOCC2)=O)=[CH:13][CH:12]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=1.NCCC1C2C(=CC=C([C:56]3[C:57]([CH3:65])([CH3:64])[C:58](=[O:63])[N:59]([CH2:61][CH3:62])[N:60]=3)C=2)NC=1C1C=C(C)C=C(C)C=1.[NH4+].[OH-]>C(Cl)Cl.CO>[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][NH:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][C:28]([NH:31][S:32]([CH3:35])(=[O:33])=[O:34])=[CH:29][CH:30]=2)=[CH:15][C:14]([C:56]2[C:57]([CH3:65])([CH3:64])[C:58](=[O:63])[N:59]([CH2:61][CH3:62])[N:60]=2)=[CH:13][CH:12]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 21249897HCID 21249897, compoundHCID 21254068HCID 21254068, compound

Product 1

HCID 21254088HCID 21254088, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent2×

Procedure

Reductive amination of 4-[4-(methanesulfonamido)phenyl] butyraldehyde (EXAMPLE 4) with 5-[3-(2-aminoethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-ethyl-4,4-dimethyl-2,4-dihydropyrazol-3-one was carried out according to the method of Example 6.2, Step F, except that 90:10 CH2Cl2-MeOH was used to develop the preparative TLC plates, while 90:10:1 CH2Cl2-MeOH-concd. NH4OH was used to extract the product. This gave a 55% yield of very pale golden-yellow glass; homogeneous by TLC in 92.5:7.5 CH2Cl2-MeOH. 500 MHz 1H NMR (CDCl3) was consistent with the assigned structure. Mass spectrum (ESI): m/e=628.5 (M+H)+.

Workup

  1. extractionto extract the product
  2. customThis gave a 55% yield of very pale golden-yellow glass

Sources & evidence

ORD record
ord-64bf14748bc54ef39795acc328e33d41
Source dataset
uspto-grants-2001_03
Patent number
US06197975B1

Reaction notes

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