Water → HCID 86590538, compound

HRID 2223504Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:13][C@H:14]([C:19]([NH:21][CH2:22][C:23]#[N:24])=[O:20])[CH2:15][CH:16]([CH3:18])[CH3:17])[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][N:35](C2C=CC(B(O)O)=CC=2)[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:23]([CH2:22][NH:21][C:19]([C@@H:14]([NH:13][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([C:2]2[CH:7]=[CH:6][C:5]([CH:37]3[CH2:36][NH:35][CH2:34][CH2:33][N:32]3[C:30]([O:29][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:31])=[CH:4][CH:3]=2)=[CH:3][CH:4]=1)[C:9]([F:12])([F:11])[F:10])[CH2:15][CH:16]([CH3:18])[CH3:17])=[O:20])#[N:24]

Participants

Conditions

Temperature: 85 °C

Procedure

To N2-[1-(4-bromophenyl)-2,2,2-trifluoroethyl]-N1-(cyanomethyl)-L-leucinamide (242 mg, 0.60 mmol), and 4-[4-(tert-butoxycarbonyl)-1-piperazinyl]phenylboronic acid (220 mg, 0.72 mmol) in DME (3 mL) under dry nitrogen was added 2M aqueous sodium carbonate (0.9 mL, 1.8 mmol) followed by the catalyst PdCl2(dppf) (63 mg, 0.077 mmol). The reaction was heated to 85° C. for 18 hours. Water was added and the product was extracted with EtOAc, the organic layer was dried over Na2SO4 and concentrated in vacuo. The crude product was purified by chromatography using EtOAc in hexane to afford tert-butyl (4′-{1-[((1S)-1-{[(cyanomethyl)amino]carbonyl}-3-methylbutyl)amino]-2,2,2-trifluroethyl}-1,1′-biphenyl-4-yl)-1-piperazinecarboxylate.

Workup

extractionthe product was extracted with EtOAc
dry with materialthe organic layer was dried over Na2SO4
concentrationconcentrated in vacuo
customThe crude product was purified by chromatography

Sources & evidence

ORD record: ord-57d78cfe8e7249568944339efaa5eeb1
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07375134B2

Reaction notes

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