Diisopropylethylamine → (5R)-3-[3-Fluoro-4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl]-5-[(4-methyl-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one

HRID 1452606Notes

Reaction equation

HRID 1452606 reaction equation
C([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][N:26]4[CH:30]=[C:29]([CH3:31])[N:28]=[N:27]4)[O:22][C:21]3=[O:32])=[CH:16][C:15]=2[F:33])[CH2:10][CH2:9]1)C1C=CC=CC=1.C(N(C(C)C)CC)(C)C.ClC(OC(Cl)=O)C.Cl.FC1C=C(N2C[C@H](CN3C=C(C)N=N3)OC2=O)C=C(F)C=1C1CCNCC=1>>[F:33][C:15]1[CH:16]=[C:17]([N:20]2[CH2:24][C@H:23]([CH2:25][N:26]3[CH:30]=[C:29]([CH3:31])[N:28]=[N:27]3)[O:22][C:21]2=[O:32])[CH:18]=[CH:19][C:14]=1[C:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=1

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 5213051-Chloroethyl chloroformateHCID 10366343(5R)-3-[4-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-3-fluorophenyl]-5-[(4-methyl-1,2,3-triazol-1-yl)methyl]oxazolidin-2-oneHCID 68879337HCID 68879337, compound

Product 1

HCID 57526968(5R)-3-[3-Fluoro-4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl]-5-[(4-methyl-1,2,3-triazol-1-yl)methyl]oxazolidin-2-oneYield 107.4%

Procedure

(5R)-3-[4-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-3-fluorophenyl]-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one (Example 43) (5.13 g, 11.46 mmol) was reacted with diisopropylethylamine (0.40 ml, 2.29 mmol) and 1-chloroethylchloroformate (1.50 ml, 13.76 mmol) as described for Intermediate 53 to give the crude title compound (4.4 g).

Sources & evidence

ORD record
ord-77b14928992d4f1cb318a0f8efbcc46e
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

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