Toluene → 3-[4-(2-Pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yl]-oxazolidin-2-one

HRID 8281Notes

Reaction equation

HRID 8281 reaction equation
O[CH2:2][CH2:3][O:4][C:5](=[O:31])[NH:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11]([C:17]3[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=4)=[N:20][N:19]4[CH2:28][CH2:29][CH2:30][C:18]=34)=[CH:12][CH:13]=[N:14]2)=[CH:9][CH:8]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>O1CCCC1>[N:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:21]1[C:17]([C:11]2[C:10]3[C:15](=[CH:16][C:7]([N:6]4[CH2:2][CH2:3][O:4][C:5]4=[O:31])=[CH:8][CH:9]=3)[N:14]=[CH:13][CH:12]=2)=[C:18]2[CH2:30][CH2:29][CH2:28][N:19]2[N:20]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 23546123HCID 23546123, compound

Product 1

HCID 102721243-[4-(2-Pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yl]-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yl]-carbamic acid 2-hydroxy-ethyl ester (40.2 mg, 0.097 mmol) and triphenylphosphine (35.0 mg, 0.14 mmol) in tetrahydrofuran (1 mL) at room temperature is added diethyl 40% azodicarboxylate in toluene (50 μL, 0.11 mmol). The mixture is stirred 18 h, filtered, and the filtrate concentrated in vacuo. The residue is chromatographed on SiO2 (2% to 15% methanol in dichloromethane) to yield the desired product, 15.2 mg (40%).

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue is chromatographed on SiO2 (2% to 15% methanol in dichloromethane)

Sources & evidence

ORD record
ord-7f5b3d00643846858bae9967fed2be37
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Reaction notes

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