Diisopropylethylamine → 2-((3R)-1-{[3-(3-chloro-4-methoxyphenyl)isoxazol-4-yl]carbonyl}piperidin-3-yl)propan-2-ol

HRID 1446359Notes

Reaction equation

HRID 1446359 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.[NH:50]1[CH2:55][CH2:54][CH2:53][C@@H:52]([C:56]([OH:59])([CH3:58])[CH3:57])[CH2:51]1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[C:14]([C:15]([N:50]3[CH2:55][CH2:54][CH2:53][C@@H:52]([C:56]([OH:59])([CH3:58])[CH3:57])[CH2:51]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 68537144(R)-2-(piperidin-3-yl)propan-2-ol hydrochloride

Product 1

HCID 591700622-((3R)-1-{[3-(3-chloro-4-methoxyphenyl)isoxazol-4-yl]carbonyl}piperidin-3-yl)propan-2-olYield 72.6%

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 2-[(3R)-piperidin-3-yl]propan-2-ol hydrochloride (7 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 (11 mg). MS (ESI, pos. ion) m/z 379 (M+1); HRMS, calcd for C19H23ClN2O4: 378.1346, found 378.1340.

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-ec231d0cbef84ffc9ef5dc26f3f71c20
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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