Trifluoroacetic acid → HCID 72513993, compound

HRID 1166773Notes

Reaction equation

HRID 1166773 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([NH:7][NH2:8])=[O:6].Br[CH2:14][CH2:15][O:16][C:17]1[C:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:23][C:20]([CH:21]=O)=[CH:19][C:18]=1[O:31][CH3:32].[CH2:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH2:36][CH2:35][NH:34]1.FC(F)(F)C(O)=O>N.CO.ClCCl>[CH2:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH2:36][CH2:35][N:34]1[CH2:14][CH2:15][O:16][C:17]1[C:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:23][C:20]([CH:21]=[N:8][NH:7][C:5](=[O:6])[C:4]2[CH:9]=[CH:10][C:11]([OH:12])=[C:2]([Cl:1])[CH:3]=2)=[CH:19][C:18]=1[O:31][CH3:32]

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 70461,2,3,4-TetrahydroisoquinolineHCID 109542683-Chloro-4-hydroxybenzohydrazideHCID 22999220HCID 22999220, compound

Product 1

HCID 72513993HCID 72513993, compound

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

This compound was prepared analogously to the compound described in the previous example starting from resin bound 3-chloro-4-hydroxybenzoic acid hydrazide (resin—[building block 1]) (2 g, ˜2 mmoles), 4-(2-bromoethoxy)-3-methoxy-5-phenylbenzaldehyde ([building block 2]) (0.93 g, 1.5 equivs.), and 1,2,3,4-tetrahydroisoquinoline ([building block 3]) (2.5 g, 10 equivs.). After cleavage with 50% trifluoroacetic acid, the residue was dissolved in 15 ml of a mixture of 25% aq. ammonia, methanol and dichloromethane (1:9:90) and purified by column chromatography on silica gel (25 g) eluting with a mixture of methanol and dichloromethane (1:12). This afforded 0.31 g of the title compound.

Workup

  1. customThis compound was prepared analogously to the compound
  2. custompurified by column chromatography on silica gel (25 g)
  3. washeluting with a mixture of methanol and dichloromethane (1:12)

Sources & evidence

ORD record
ord-2597783c114d40bb997e6d069c2894e3
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

Loading…