1,2-Dichloroethane → HCID 89541511, compound

HRID 1504313Notes

Reaction equation

HRID 1504313 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([OH:22])=O)=[CH:16][N:15]=2)[C@H:10]([CH3:23])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.[CH3:38][C:39]1([CH3:53])[C:43]([CH3:45])([CH3:44])[O:42][B:41]([C:46]2[CH:52]=[CH:51][C:49]([NH2:50])=[CH:48][CH:47]=2)[O:40]1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:22])[NH:50][C:49]3[CH:48]=[CH:47][C:46]([B:41]4[O:42][C:43]([CH3:45])([CH3:44])[C:39]([CH3:53])([CH3:38])[O:40]4)=[CH:52][CH:51]=3)=[CH:16][N:15]=2)[C@H:10]([CH3:23])[CH2:9]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 67495464HCID 67495464, compound

Product 1

HCID 89541511HCID 89541511, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (R)-4-(5-carboxy-pyridin-2-yl)-3-methyl-piperazine-1-carboxylic acid tert-butyl ester (200 mg, 0.6 mmol) and EDC (140 mg, 0.75 mmol) and HOAt (100 mg, 0.75 mmol) dissolved in DMF (4.6 mL) was stirred for 30 min and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (140 mg, 0.62 mmol) and N,N-diisopropylethylamine (130 μL, 0.75 mmol) were added. The reaction mixture was stirred at RT overnight and extracted with ethyl acetate/water. The organic layer was dried over sodium sulfate, filtered, concentrated, and purified by silica gel chromatography (eluted with 0-70% ethyl acetate:hexanes) to provide the title intermediate (250 mg, 80% yield). (m/z): [M+H]+ calcd for C28H39BN4O5 523.30. found 523.5.

Workup

  1. stirringThe reaction mixture was stirred at RT overnight
  2. extractionextracted with ethyl acetate/water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography (eluted with 0-70% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-068e58bf210943b094084f50504f1b1a
Source dataset
uspto-grants-2015_12
Patent number
US09212168B2

Reaction notes

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