Trifluoroacetic acid → HCID 21101684, compound

HRID 1353500Notes

Reaction equation

HRID 1353500 reaction equation
C(O[C:6]([N:8]([CH3:25])[CH:9]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]3[C:18](=[CH:19][C:20]([Cl:24])=[CH:21][CH:22]=3)[N:17]=[CH:16][CH:15]=2)[CH2:10]1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O.[F:33][C:34]1[CH:39]=[CH:38][C:37]([N:40]=C=O)=[CH:36][CH:35]=1.C(N(CC)CC)C>C(Cl)Cl>[F:33][C:34]1[CH:39]=[CH:38][C:37]([NH:40][C:6]([N:8]([CH3:25])[CH:9]2[CH2:13][CH2:12][N:11]([C:14]3[C:23]4[C:18](=[CH:19][C:20]([Cl:24])=[CH:21][CH:22]=4)[N:17]=[CH:16][CH:15]=3)[CH2:10]2)=[O:7])=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 709554-Fluorophenyl isocyanateHCID 21101686HCID 21101686, compound

Product 1

HCID 21101684HCID 21101684, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-[3-[tert-butoxycarbonyl(methyl)amino]pyrrolidin1-yl]-7-chloroquinoline (285 mg, 0.79 mmol) in CH2Cl2 (5 mL) is treated with trifluoroacetic acid (1 mL). After 1 h the reaction mixture is concentrated. The residue is dissolved in CH2Cl2 (10 mL), and 4-fluorophenyl isocyanate (90 μL, 0.79 mmol) and triethylamine (1 mL) are added. The reaction mixture is concentrated, and the residue is purified by column chromatography and an aqueous work-up step yielding the title product.

Workup

  1. concentrationAfter 1 h the reaction mixture is concentrated
  2. dissolutionThe residue is dissolved in CH2Cl2 (10 mL)
  3. concentrationThe reaction mixture is concentrated
  4. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-8c8c01754c254121a3dcb837607f584e
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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