3,5-Bis(trifluoromethyl)benzyl bromide → HCID 86613817, compound

HRID 2378139Notes

Reaction equation

HRID 2378139 reaction equation
C1(N2C3C(=NC(OC)=CC=3)C(NC(=O)C)CC2C)CCCC1.[CH:23]([O:26][C:27]([N:29]1[CH:38]([CH2:39]C)[CH:37]([CH3:41])[CH:36]([NH:42][C:43]2[CH:44]=[N:45][C:46]3[CH2:47][CH2:48][CH2:49][CH2:50][C:51]=3[CH:52]=2)[C:35]2[N:34]=[C:33]3[CH2:53][CH2:54][CH2:55][CH2:56][C:32]3=[CH:31][C:30]1=2)=[O:28])([CH3:25])[CH3:24].[F:57][C:58]([F:72])([F:71])[C:59]1[CH:60]=[C:61]([CH:64]=[C:65]([C:67]([F:70])([F:69])[F:68])[CH:66]=1)[CH2:62]Br.C[Si](C)(C)[N-][Si](C)(C)C.[Li+]>>[CH:23]([O:26][C:27]([N:29]1[CH:38]([CH3:39])[CH:37]([CH3:41])[CH:36]([N:42]([CH2:62][C:61]2[CH:64]=[C:65]([C:67]([F:69])([F:70])[F:68])[CH:66]=[C:59]([C:58]([F:57])([F:71])[F:72])[CH:60]=2)[C:43]2[CH:44]=[N:45][C:46]3[CH2:47][CH2:48][CH2:49][CH2:50][C:51]=3[CH:52]=2)[C:35]2[N:34]=[C:33]3[CH2:53][CH2:54][CH2:55][CH2:56][C:32]3=[CH:31][C:30]1=2)=[O:28])([CH3:24])[CH3:25]

Participants

5

Reactant 4

HCID 1225733,5-Bis(trifluoromethyl)benzyl bromideHCID 2733832Lithium HexamethyldisilazideHCID 58926753HCID 58926753, compoundHCID 69643684HCID 69643684, compound

Product 1

HCID 86613817HCID 86613817, compoundYield 20%

Procedure

Prepare the title compound by essentially following the procedure described in Example 49, Step 2, by replacing (+/−)-N-(1-cyclopentyl-6-methoxy-2-methyl-1,2,3,4-tetrahydro-[1,5]napthyridin-4-yl)-acetamide, with 2-ethyl-3-methyl-4-(5,6,7,8-tetrahydro-quinolin-3-ylamino)-3,4,6,7,8,9-hexahydro-2H-benzo[b][1,5]napthyridine-1-carboxylic acid isopropyl ester (0.175 g, 0.378 mmol), and using 3,5-bis trifluoromethyl benzyl bromide and lithium hexamethyldisilazide. Purify using silica gel column chromatography (gradient eluent, 50:50 ethyl acetate in hexane) to afford the title compound (0.052 g, 20%). MS (ES+): 689 (M+H).

Workup

  1. customPurify

Sources & evidence

ORD record
ord-8fa763191991478e81880f33c404c7f1
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

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