Diisopropylethylamine → N-[(4-fluoro-3'-{[(3S)-3-methyl-1-piperazinyl]methyl}-3-biphenylyl)methyl]-3-(4-piperidinyl)benzamide

HRID 2080316Notes

Reaction equation

HRID 2080316 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][N:17]3[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[C@@H:19]([CH3:30])[CH2:18]3)[CH:11]=2)[CH:6]=[CH:7][C:8]=1[F:9].[NH:31]1[CH2:36][CH2:35][CH:34]([C:37]2[CH:38]=[C:39]([CH:43]=[CH:44][CH:45]=2)[C:40](O)=[O:41])[CH2:33][CH2:32]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C>[F:9][C:8]1[CH:7]=[CH:6][C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][N:17]3[CH2:22][CH2:21][NH:20][C@@H:19]([CH3:30])[CH2:18]3)[CH:11]=2)=[CH:4][C:3]=1[CH2:2][NH:1][C:40](=[O:41])[C:39]1[CH:43]=[CH:44][CH:45]=[C:37]([CH:34]2[CH2:33][CH2:32][NH:31][CH2:36][CH2:35]2)[CH:38]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 404283063-(Piperidin-4-yl)benzoic acidHCID 577367151,1-Dimethylethyl (2S)-4-{[3'-(aminomethyl)-4'-fluoro-3-biphenylyl]methyl}-2-methyl-1-piperazinecarboxylate

Product 1

HCID 11649025N-[(4-fluoro-3'-{[(3S)-3-methyl-1-piperazinyl]methyl}-3-biphenylyl)methyl]-3-(4-piperidinyl)benzamideYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the procedure outlined in Example 40, 1,1-dimethylethyl (2S)-4-{[3′-(aminomethyl)-4′-fluoro-3-biphenylyl]methyl}-2-methyl-1-piperazinecarboxylate (0.100 g, 0.242 mmol), 3-(4-piperidinyl)benzoic acid (0.074 g, 0.243 mmol), HATU (0.103 g, 0.271 mmol), and diisopropylethylamine (0.10 mL, 0.574 mmol) in DMF (2.5 mL) were reacted to give the desired product (0.024 g, 21.0%). EI-MS m/z 501 (M−H)+.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-9464d98d82954f1d920ec9306a020315
Source dataset
uspto-grants-2011_04
Patent number
US07932247B2

Reaction notes

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