Ammonia → HCID 19696451, compound

HRID 863696Notes

Reaction equation

HRID 863696 reaction equation
[C:1]([O:4][CH2:5][CH:6]1[CH2:36][CH2:35][CH2:34][N:9]2[C:10]3[C:15]([C:16]([C:17]4[C:18](=O)[O:19][C:20](=[O:32])[C:21]=4[C:22]4[C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[N:24]([CH3:31])[CH:23]=4)=[C:8]2[CH2:7]1)=[CH:14][CH:13]=[CH:12][CH:11]=3)(=[O:3])[CH3:2].[N:37]1C(C)=CC=CC=1C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[NH3:60]>ClCCl>[C:1]([OH:4])(=[O:3])[CH3:2].[NH2:60][CH2:5][CH:6]1[CH2:36][CH2:35][CH2:34][N:9]2[C:10]3[C:15]([C:16]([C:17]4[C:18](=[O:19])[NH:37][C:20](=[O:32])[C:21]=4[C:22]4[C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[N:24]([CH3:31])[CH:23]=4)=[C:8]2[CH2:7]1)=[CH:14][CH:13]=[CH:12][CH:11]=3

Participants

6

Reactant 4

HCID 222AmmoniaHCID 79372,6-LutidineHCID 67749Trifluoromethanesulfonic anhydrideHCID 10028207HCID 10028207, compound

Product 1

HCID 19696451HCID 19696451, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 150 mg of the product of Example 49 and 146 mg of 2,6-lutidine in 15 ml of dichloromethane was added to a solution of 290 mg of trifluoromethanesulfonic anhydride at 0° C. After 3 hours, 25 ml of 33% aqueous ammonia were added and the mixture was stirred for 16 hours. The mixture was extracted with dichloromethane and the combined extracts were dried and concentrated. Chromatography of the residue on silica gel with dichloromethane/methanol/acetic acid/water (90:18:3:2) gave 50 mg of 3-[9-(aminomethyl)-7,8,9,10-tetrahydro-6H-azepino[1,2-a]indol-11-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione acetate of melting point 215° C. (decomposition).

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. customthe combined extracts were dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-aea3b2fd66484e9b979c81f914ad58f7
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

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