Trifluoroacetic acid → HCID 21101690, compound

HRID 1353320Notes

Reaction equation

HRID 1353320 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]3[C:18](=[CH:19][C:20]4[O:26][CH2:25][O:24][C:21]=4[CH:22]=3)[N:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O.C(OC(N1CCNCC1)=O)(C)(C)C.[F:47][C:48]1[CH:53]=[CH:52][C:51]([N:54]=C=O)=[CH:50][CH:49]=1>C(Cl)Cl.C(N(CC)CC)C>[F:47][C:48]1[CH:53]=[CH:52][C:51]([NH:54][C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[C:23]4[C:18](=[CH:19][C:20]5[O:26][CH2:25][O:24][C:21]=5[CH:22]=4)[N:17]=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)=[O:7])=[CH:50][CH:49]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 709554-Fluorophenyl isocyanateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 21101942HCID 21101942, compound

Product 1

HCID 21101690HCID 21101690, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

4-Chloro-6,7-methylenedioxyquinoline [obtained from 3,4-methylendioxyaniline following the protocol of Krogstad et. al. (De, D., Byers L. D., Krogstad, D. J. J. Heterocyclic Chem. 1997, 34, 315; 1H NMR ([D]6-DMSO), δ 6.28 (s, 2H), 7.45 (s, 1H), 7.50 (s, 1H), 7.65 (d, 1H), 8.62 (d, 1H)) (0.50 g, 2.4 mmol) and 1-tert-butoxycarbonylpiperazine (1.8 g, 9.6 mmol) are reacted according to method A yielding 391 mg of 4-[4-(tert-butoxycarbonyl)piperazin-1-yl]-6,7-methylenedioxy quinoline. After cleaving the Boc group with trifluoroacetic acid (1.5 mL) in CH2Cl2 (1.5 mL), the piperazine is treated with 4-fluorophenylisocyanate (86 μL) and triethylamine (0.245 mL) according to method C yielding the title product.

Workup

  1. customare reacted

Sources & evidence

ORD record
ord-ab010640e76d4eb8bdd4bf0ed0a43fa7
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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