Diisopropylethylamine → 1-{[3-(3-Chloro-4-methoxyphenyl)isoxazol-4-yl]carbonyl}-3-(4-fluoro-3-methylphenyl)pyrrolidin-3-ol

HRID 1446355Notes

Reaction equation

HRID 1446355 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[C:14]([C:15]([OH:17])=O)=[CH:13][O:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C(N(C(C)C)C(C)C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.[F:50][C:51]1[CH:56]=[CH:55][C:54]([C:57]2([OH:62])[CH2:61][CH2:60][NH:59][CH2:58]2)=[CH:53][C:52]=1[CH3:63]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[C:14]([C:15]([N:59]3[CH2:60][CH2:61][C:57]([C:54]4[CH:55]=[CH:56][C:51]([F:50])=[C:52]([CH3:63])[CH:53]=4)([OH:62])[CH2:58]3)=[O:17])=[CH:13][O:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 591701453-(3-Chloro-4-methoxyphenyl)-isoxazole-4-carboxylic acidHCID 686855673-(4-Fluoro-3-methylphenyl)pyrrolidin-3-ol hydrochloride

Product 1

HCID 591701811-{[3-(3-Chloro-4-methoxyphenyl)isoxazol-4-yl]carbonyl}-3-(4-fluoro-3-methylphenyl)pyrrolidin-3-olYield 40.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(3-chloro-4-methoxyphenyl)isoxazole-4-carboxylic acid (10 mg, 0.04 mmol), N-ethyl-N-isopropylpropan-2-amine (14 μL, 0.08 mmol, 2 equ.) and TBTU (15 mg, 0.046 mmol, 1.2 equ.) in DMF (0.3 mL) was added to 3-(4-fluoro-3-methylphenyl)pyrrolidin-3-ol hydrochloride (9 mg, 0.04 mmol). After 1 h at rt the crude product was purified by RP-HPLC, evaporated and dried in vacuum to yield the title compound (7 mg). MS (ESI, pos. ion) m/z: calcd for C22H20ClFN2O4: 430.1096, found 430.1094.

Workup

  1. customAfter 1 h at rt the crude product was purified by RP-HPLC
  2. customevaporated
  3. customdried in vacuum

Sources & evidence

ORD record
ord-c5c38f03c0d245faa0181572752ac5ae
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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