Trifluoroacetic acid → HCID 88213892, compound

HRID 1066349Notes

Reaction equation

HRID 1066349 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]([NH:16][CH2:17][CH2:18][NH:19][C:20]1[C:21]3[C:26]([N:27]=[C:28]4[C:33]=1[CH:32]=[C:31]([O:34][CH2:35][C:36]([O:38]C(C)(C)C)=[O:37])[CH:30]=[CH:29]4)=[CH:25][C:24]([Cl:43])=[CH:23][CH:22]=3)=[C:11]1[C:6]([CH:7]=[CH:8][C:9]([O:44][CH2:45][C:46]([O:48]C(C)(C)C)=[O:47])=[CH:10]1)=[N:5]2.[F:53][C:54]([F:59])([F:58])[C:55]([OH:57])=[O:56]>ClCCl>[F:53][C:54]([F:59])([F:58])[C:55]([OH:57])=[O:56].[F:53][C:54]([F:59])([F:58])[C:55]([OH:57])=[O:56].[Cl:43][C:24]1[CH:25]=[C:26]2[C:21](=[CH:22][CH:23]=1)[C:20]([NH:19][CH2:18][CH2:17][NH:16][C:12]1[C:13]3[C:4]([N:5]=[C:6]4[C:11]=1[CH:10]=[C:9]([O:44][CH2:45][C:46]([OH:48])=[O:47])[CH:8]=[CH:7]4)=[CH:3][C:2]([Cl:1])=[CH:15][CH:14]=3)=[C:33]1[C:28]([CH:29]=[CH:30][C:31]([O:34][CH2:35][C:36]([OH:38])=[O:37])=[CH:32]1)=[N:27]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21198477HCID 21198477, compound

Product 1

HCID 88213892HCID 88213892, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N,N′-bis[6-chloro-2-(tert-butoxycarbonyl)methoxy-9-acridinyl]-1,2-ethanediamine (12 mg, 0.12 mmol) and trifluoroacetic acid (5 mL) in dichloromethane (12 mL) was stirred at RT for 18 h. The reaction mixture was concentrated in vacuo and the residue was purified by HPLC (YMC ODS-AQ, 100×250 mm, 80 mL/min, 26% acetonitrile/water/0.1% trifluoroacetic acid, UV detection at 254 nm) to give the title compound as a yellow solid. MS(ES) m/e 631.3 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by HPLC (YMC ODS-AQ, 100×250 mm, 80 mL/min, 26% acetonitrile/water/0.1% trifluoroacetic acid, UV detection at 254 nm)

Sources & evidence

ORD record
ord-e28e435cda594265ae700a5da4bf9eef
Source dataset
uspto-grants-2001_06
Patent number
US06242459B1

Reaction notes

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