Ammonia → HCID 178480014, compound

HRID 345681Notes

Reaction equation

HRID 345681 reaction equation
[C:1]([N:3]=[C:4](SC)[NH:5][CH2:6][CH2:7][CH2:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18]2[C:19](=[O:34])[NH:20][C:21](=[O:33])[C:22]=2[C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]([CH3:32])[CH:24]=2)=[CH:10]1)#[N:2].C[N:38](C=O)C.N>C(O)C>[C:1]([N:3]=[C:4]([NH2:38])[NH:5][CH2:6][CH2:7][CH2:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18]2[C:19](=[O:34])[NH:20][C:21](=[O:33])[C:22]=2[C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]([CH3:32])[CH:24]=2)=[CH:10]1)#[N:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6228DimethylformamideHCID 178503916HCID 178503916, compound

Product 1

HCID 178480014HCID 178480014, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

100 mg of the product of Example 50 were heated with 30 ml of ethanol, 2 ml of DMF and 40 ml of a saturated solution of ammonia in ethanol at 100° C. for 16 hours. The solvents were removed under reduced pressure and the residue was chromatographed on silica gel with 1% methanol in dichloromethane to give 10 mg of 3-[1-[3-(2-cyanoguanidino)propyl]-3-indolyl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione, m.p. 168°-170° C.

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe residue was chromatographed on silica gel with 1% methanol in dichloromethane

Sources & evidence

ORD record
ord-84c9ba96b36a458e92d87c6daa5f7732
Source dataset
uspto-grants-1991_10
Patent number
US05057614

Reaction notes

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