4-Chlorobenzylamine → HCID 76542822, compound

HRID 1361033Notes

Reaction equation

HRID 1361033 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[C:4](=[CH:8][C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:18][C:19]([OH:21])=O)[CH:10]=2)[S:3]1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[Cl:44][C:45]1[CH:52]=[CH:51][C:48]([CH2:49][NH2:50])=[CH:47][CH:46]=1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1.C(OCC)(=O)C>[Cl:44][C:45]1[CH:52]=[CH:51][C:48]([CH2:49][NH:50][C:19](=[O:21])[CH2:18][N:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:9]([CH:8]=[C:4]3[S:3][C:2](=[O:1])[NH:6][C:5]3=[O:7])=[CH:10]2)=[CH:47][CH:46]=1

Participants

8

Reactant 5

HCID 660364-ChlorobenzylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 76545901HCID 76545901, compound

Product 1

HCID 76542822HCID 76542822, compoundYield 58.7%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent3×

Procedure

[3-(2,4-Dioxothiazolidin-5-ylidenemethyl)indol-1-yl]acetic acid (example 300, 90.7 mg, 0.3 mmol) was dissolved in NMP (1 mL) and added to a mixture of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, hydrochloride (86.4 mg, 0.45 mmol) and 1-hydroxybenzotriazol (68.8 mg, 0.45 mmol) in NMP (1 mL). The resulting mixture was shaken at RT for 2 h. 4-Chlorobenzylamine (51 mg, 0.36 mmol) and DIPEA (46.4 mg, 0.36 mmol) in NMP (1 mL) were added to the mixture resulting mixture shaken at RT for 2 days. Subsequently ethyl acetate (10 mL) was added and the resulting mixture washed with 2×10 mL water followed by saturated ammonium chloride (5 mL). The organic phase was evaporated to dryness giving 75 mg (57%) of the title compound.

Workup

  1. customresulting mixture
  2. stirringshaken at RT for 2 days
  3. washthe resulting mixture washed with 2×10 mL water
  4. customThe organic phase was evaporated to dryness

Sources & evidence

ORD record
ord-c4df5ed8dc014e6ea244c4cd7fa0ed67
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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