PyBOP → 7-[(3RS,5SR)-3,5-Dimethylpiperazin-1-yl]-6-fluoro-8-methoxy-N-[2-methyl-4-(trifluoromethoxy)benzyl]-4-oxo-1-(2,2,2-trifluoroethyl)-1,4-dihydroquinoline-3-carboxamide

HRID 251860Notes

Reaction equation

HRID 251860 reaction equation
[CH3:1][CH:2]1[NH:7][CH:6]([CH3:8])[CH2:5][N:4]([C:9]2[C:18]([O:19][CH3:20])=[C:17]3[C:12]([C:13](=[O:29])[C:14]([C:26](O)=[O:27])=[CH:15][N:16]3[CH2:21][C:22]([F:25])([F:24])[F:23])=[CH:11][C:10]=2[F:30])[CH2:3]1.[CH3:31][C:32]1[CH:39]=[C:38]([O:40][C:41]([F:44])([F:43])[F:42])[CH:37]=[CH:36][C:33]=1[CH2:34][NH2:35].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C)C1C=CN=CC=1.CN(C=O)C>[CH3:8][CH:6]1[NH:7][CH:2]([CH3:1])[CH2:3][N:4]([C:9]2[C:18]([O:19][CH3:20])=[C:17]3[C:12]([C:13](=[O:29])[C:14]([C:26]([NH:35][CH2:34][C:33]4[CH:36]=[CH:37][C:38]([O:40][C:41]([F:42])([F:43])[F:44])=[CH:39][C:32]=4[CH3:31])=[O:27])=[CH:15][N:16]3[CH2:21][C:22]([F:25])([F:23])[F:24])=[CH:11][C:10]=2[F:30])[CH2:5]1

Participants

6

Reactant 3

HCID 2724699PyBOPHCID 577941232-Methyl-4-(trifluoromethoxy)benzylamineHCID 668607847-[(3RS,5SR)-3,5-dimethylpiperazin-1-yl]-6-fluoro-8-methoxy-4-oxo-1-(2,2,2-trifluoroethyl)-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 724938447-[(3RS,5SR)-3,5-Dimethylpiperazin-1-yl]-6-fluoro-8-methoxy-N-[2-methyl-4-(trifluoromethoxy)benzyl]-4-oxo-1-(2,2,2-trifluoroethyl)-1,4-dihydroquinoline-3-carboxamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

212 mg (0.49 mmol) of 7-[(3RS,5SR)-3,5-dimethylpiperazin-1-yl]-6-fluoro-8-methoxy-4-oxo-1-(2,2,2-trifluoroethyl)-1,4-dihydroquinoline-3-carboxylic acid (salt free compound of Example 50A) and 366 mg (0.98 mmol) of 2-methyl-4-trifluoromethoxybenzylamine (Example 69A) are dissolved together with 357 mg (0.69 mmol) of PyBOP and 30 mg (0.25 mmol) of 4-dimethylaminopyridine in 4 ml of DMF and stirred for 12 h at room temperature. The reaction mixture is then purified by preparative HPLC (Method 7). A solid is obtained. Yield: 170 mg (56% of theory).

Workup

  1. customThe reaction mixture is then purified by preparative HPLC (Method 7)
  2. customA solid is obtained

Sources & evidence

ORD record
ord-71c71a3d65ca4906a6c4aa4b042a8e66
Source dataset
uspto-grants-2011_01
Patent number
US07867992B2

Reaction notes

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