HCID 59536015, compound → HCID 59536093, compound

HRID 1944626Notes

Reaction equation

HRID 1944626 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:26]([O:28]C(C)(C)C)=[O:27])=[C:10]([NH:13][C:14]([N:16]3[CH2:25][CH2:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:17]3)=[O:15])[S:11][CH:12]=2)=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:26]([OH:28])=[O:27])=[C:10]([NH:13][C:14]([N:16]3[CH2:25][CH2:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:17]3)=[O:15])[S:11][CH:12]=2)=[CH:4][CH:3]=1.[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([NH:13][C:14]([N:16]3[CH2:25][CH2:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:17]3)=[O:15])[S:11][CH:12]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 59536015HCID 59536015, compound

Product 2

HCID 59536077HCID 59536077, compoundYield 16.3%HCID 59536093HCID 59536093, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of tert-butyl 4-(4-bromophenyl)-2-(2-1,2,3,4-tetrahydroisoquinolylcarbonylamino)thiophene-3-carboxylate (70) (46.3 mg) in TFA/DCM (1:1, 3 ml) was stirred at r.t. for 40 min. After evaporated to dryness, the residue was dissolved in DMF and then subjected to reverse phase prep HPLC purification. 22.9 mg 4-(4-bromophenyl)-2-(2-1,2,3,4-tetrahydroisoquinolylcarbonylamino)thiophene-3-carboxylic acid (71A) (yield: 55.5%) and 6.1 mg N-[4-(4-bromophenyl)(2-thienyl)]-2-1,2,3,4-tetrahydroisoquinolylcarboxamide (71B) (yield: 16.3%) were isolated as white solids respectively.

Workup

  1. customAfter evaporated to dryness
  2. dissolutionthe residue was dissolved in DMF
  3. customphase prep HPLC purification

Sources & evidence

ORD record
ord-812638e7230d4227a8779bb62f68e766
Source dataset
uspto-grants-2013_03
Patent number
US08394848B2

Reaction notes

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