HCID 18367903, compound → HCID 18368214, compound

HRID 379904Notes

Reaction equation

HRID 379904 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:3]=1[C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[NH:15][C:16](=[O:19])[CH2:17][CH3:18])=[CH:12][CH:11]=[C:10]([Cl:20])[CH:9]=2)=[O:5]>Cl.CO>[ClH:20].[NH2:1][C:2]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:3]=1[C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[NH:15][C:16](=[O:19])[CH2:17][CH3:18])=[CH:12][CH:11]=[C:10]([Cl:20])[CH:9]=2)=[O:5]

Participants

3

Reactant 1

HCID 18367903HCID 18367903, compound

Product 1

HCID 18368214HCID 18368214, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

2-(2-Amino-5-chlorobenzoyl)-6-chloro-3-(propionylamino)indole (Example 389, 394 mg) was dissolved in 10% HCl-methanol (10 ml) and the solvent was removed. The residue was crystallized from ethyl acetate/ethanol to give 175 mg (41%) of the title compound. m.p.: 184-185° C. IR(KBr)ν: 3200, 1618, 1541, 1491, 1321, 1232, 1061, 920 cm−1 1H-NMR (DMSO-d6) δ: 11.70 (1 H, br s), 9.79 (1 H, br s), 7.59 (2 H, br d, J=8.6 Hz), 7.44 (1 H, d, J=1.6 Hz), 7.36 (1 H, d, J=2.5 Hz), 7.28 (1 H, dd, J=2.5, 8.7 Hz), 7.10 (1 H, dd, J=1.6, 8.6 Hz), 6.85 (1 H, d, J=8.7 Hz), 2.12 (2 H, q, J=7.6 Hz), 0.89 (3 H, t, J=7.6 Hz).

Workup

  1. customthe solvent was removed
  2. customThe residue was crystallized from ethyl acetate/ethanol

Sources & evidence

ORD record
ord-5fec3d94d9334c40ad4f9cdf34aeadaf
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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