Thiourea → 3-(3-(4-(1-methyl-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)-1H-indol-1-yl)propyl carbamimidothioate methanesulfonate

HRID 345701Notes

Reaction equation

HRID 345701 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:34])[NH:13][C:14](=[O:33])[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][O:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH:17]=2)=[CH:3]1.[NH2:35][C:36]([NH2:38])=[S:37]>C(O)C>[CH3:32][S:29]([OH:31])(=[O:30])=[O:28].[C:36]([S:37][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:33])[NH:13][C:12](=[O:34])[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)(=[NH:38])[NH2:35]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 151630513-(1-methyl-3-indolyl)-4-[1-[3-(methylsulphonyloxy)propyl]-3-indolyl]-1H-pyrrole-2,5-dione

Product 1

HCID 116282053-(3-(4-(1-methyl-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)-1H-indol-1-yl)propyl carbamimidothioate methanesulfonateYield 78.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.455 g of the product of Example 58 in 45 ml of ethanol were treated with 364 mg of thiourea and the mixture was heated at reflux for 18 hours. After cooling the precipitate was filtered off and washed with ethanol and with diethyl ether. The solid was dried to give 1.33 g of 3-[1-[3-(amidinothio)propyl]-3-indolyl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione methanesulphonate, m.p. 236°-238° C. (decomposition).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 18 hours
  3. temperatureAfter cooling the precipitate
  4. filtrationwas filtered off
  5. washwashed with ethanol and with diethyl ether
  6. customThe solid was dried

Sources & evidence

ORD record
ord-6e0b4cb54f0c41f9b2999bbdcdc5c8b3
Source dataset
uspto-grants-1991_10
Patent number
US05057614

Reaction notes

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