Acetylglycine → HCID 70223399, compound

HRID 1531552Notes

Reaction equation

HRID 1531552 reaction equation
[C:1]([NH:4][CH2:5][C:6]([OH:8])=O)(=[O:3])[CH3:2].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH2:31]([N:38]([CH2:59][CH2:60][CH2:61][CH2:62][C:63]1[CH:68]=[CH:67][C:66]([N+:69]([O-:71])=[O:70])=[CH:65][CH:64]=1)[CH2:39][CH2:40][C:41]1[C:49]2[C:44](=[CH:45][CH:46]=[C:47]([NH2:50])[CH:48]=2)[NH:43][C:42]=1[C:51]1[CH:56]=[C:55]([CH3:57])[CH:54]=[C:53]([CH3:58])[CH:52]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>>[CH2:31]([N:38]([CH2:59][CH2:60][CH2:61][CH2:62][C:63]1[CH:68]=[CH:67][C:66]([N+:69]([O-:71])=[O:70])=[CH:65][CH:64]=1)[CH2:39][CH2:40][C:41]1[C:49]2[C:44](=[CH:45][CH:46]=[C:47]([NH:50][C:6]([CH2:5][NH:4][C:1](=[O:3])[CH3:2])=[O:8])[CH:48]=2)[NH:43][C:42]=1[C:51]1[CH:52]=[C:53]([CH3:58])[CH:54]=[C:55]([CH3:57])[CH:56]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

5

Reactant 4

HCID 10972AcetylglycineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21254098HCID 21254098, compound

Product 1

HCID 70223399HCID 70223399, compoundYield 92.4%

Procedure

To a solution of acetylaminoacetic acid (32.2 mg in 6 mL dry methylene chloride) was added 48 mg 1-hydroxybenzotriazole followed by 50 mg 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and the mixture stirred at room temperature. After 50 minutes, a solution of 3-(2-{benzyl-[4-(4-nitrophenyl)butyl]amino}ethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-ylamine (120 mg in 2 mL methylene chloride) was added and stirring continued. After 4 hours (total), the mixture was concentrated in vacuo and purified by flash chromatography on silica gel (methylene chloride:methanol, 95:5) to give the title compound (131 mg).

Workup

  1. stirringstirring
  2. waitAfter 4 hours (total)
  3. concentrationthe mixture was concentrated in vacuo
  4. custompurified by flash chromatography on silica gel (methylene chloride:methanol, 95:5)

Sources & evidence

ORD record
ord-86756120c0684aacace07c6fe676ade2
Source dataset
uspto-grants-2001_03
Patent number
US06197975B1

Reaction notes

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