Trifluoroacetic acid → HCID 21101692, compound

HRID 1353321Notes

Reaction equation

HRID 1353321 reaction equation
C([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]3[C:18](=[CH:19][C:20]([CH3:24])=[CH:21][CH:22]=3)[N:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28].C(OC(N1CCNCC1)=O)(C)(C)C.[F:45][C:46]1[CH:51]=[CH:50][C:49]([N:52]=C=O)=[CH:48][CH:47]=1>C(Cl)Cl.C(N(CC)CC)C>[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28].[F:45][C:46]1[CH:51]=[CH:50][C:49]([NH:52][C:6]([N:8]2[CH2:9][CH2:10][N:11]([C:14]3[C:23]4[C:18](=[CH:19][C:20]([CH3:24])=[CH:21][CH:22]=4)[N:17]=[CH:16][CH:15]=3)[CH2:12][CH2:13]2)=[O:5])=[CH:48][CH:47]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 709554-Fluorophenyl isocyanateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 21101949HCID 21101949, compound

Product 1

HCID 21101692HCID 21101692, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

4-Chloro-7-methylquinoline [obtained from 3-toluidine 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 2.55 (s, 3H), 7.60 (m, 1H), 7.75 (d, 1H), 7.90 (s, 1H), 8.10 (d, 1H), 8.80 (d, 1H)) (0.80 g, 4.5 mmol) and 1-tert-butoxycarbonylpiperazine (3.35 g, 18 mmol) are reacted according to method A yielding 475 mg of 4-[4-(tert-butoxycarbonyl)piperazin-1-yl]-7-methylquinoline. After cleaving the Boc group with trifluoroacetic acid (1.8 mL) in CH2Cl2 (1.8 mL), the piperazine is treated with 4-fluorophenyl isocyanate and triethylamine (0.245 mL) according to method C yielding the title product.

Workup

  1. customare reacted

Sources & evidence

ORD record
ord-623956871e9f429ebb40607e07cfc690
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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