Trifluoroacetic acid → HCID 73113646, compound

HRID 1166772Notes

Reaction equation

HRID 1166772 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]([O:25][CH3:26])=[CH:23][C:20]([CH:21]=O)=[CH:19][C:18]=1[Cl:27].[CH2:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:31][CH2:30][NH:29]1.FC(F)(F)C(O)=O>N.CO.ClCCl>[Cl:27][C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([O:25][CH3:26])[C:17]=1[O:16][CH2:15][CH2:14][N:29]1[CH2:30][CH2:31][C:32]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:28]1)[CH:21]=[N:8][NH:7][C:5](=[O:6])[C:4]1[CH:9]=[CH:10][C:11]([OH:12])=[C:2]([Cl:1])[CH:3]=1

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 70461,2,3,4-TetrahydroisoquinolineHCID 109542683-Chloro-4-hydroxybenzohydrazideHCID 22999110HCID 22999110, compound

Product 1

HCID 73113646HCID 73113646, 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-chloro-5-methoxybenzaldehyde ([building block 2]) (0.81 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 (1.0 g) 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 0.11 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-b0940c8ddaf64fe1b7925103956344f2
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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