Ammonia → HCID 70291580, compound

HRID 345676Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:37])[NH:13][C:14](=[O:36])[C:15]=2[C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH2:25][CH2:26][CH2:27][NH:28][C:29](SC)=[CH:30][N+:31]([O-:33])=[O:32])[CH:17]=2)=[CH:3]1.[NH3:38]>C(O)C>[NH2:38][C:29]([NH:28][CH2:27][CH2:26][CH2:25][N:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]([C:15]2[C:14](=[O:36])[NH:13][C:12](=[O:37])[C:11]=2[C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:2]([CH3:1])[CH:3]=2)=[CH:17]1)=[CH:30][N+:31]([O-:33])=[O:32]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 128 mg of the product of Example 51 in 30 ml of ethanol was treated with 10 ml of a saturated solution of ammonia in ethanol and the mixture was heated at 80° C. for 3 hours. The solvent was removed under reduced pressure and the residue was chromatographed on silica gel with 10% methanol in dichloromethane to give 39 mg of 3-[1-[3-(1-amino-2-nitrovinylamino)propyl]-3-indolyl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione, m.p. 206°-209° C. (decomposition).

Workup

customThe solvent was removed under reduced pressure
customthe residue was chromatographed on silica gel with 10% methanol in dichloromethane

Sources & evidence

ORD record: ord-286e5ed873c24007a9b4723db198de95
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05057614

Reaction notes

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