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1,2-Dichloroethane → N-4-Isoxazolyl-2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzamide

HRID 1623804
Notes
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Reaction equation

HRID 1623804 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[CH:14][C:10]=2[C:11](O)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)CCl.C1C=C[C:31]2[N:36]([OH:37])N=[N:34][C:32]=2[CH:33]=1.O1C=C(N)C=N1>CN(C)C=O.O>[O:37]1[CH:33]=[C:32]([NH:34][C:11](=[O:12])[C:10]2[CH:14]=[C:15]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[CH:16]=[CH:17][C:9]=2[O:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:31]=[N:36]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 138042781,2-Oxazol-4-amineHCID 669904822-(Benzyloxy)-5-(pyridin-4-yl)benzoic acid

Product 1

HCID 68108909N-4-Isoxazolyl-2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzamide

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzoic acid (may be prepared as described in Description 79; 100 mg, 0.30 mmol), EDC (172 mg, 0.90 mmol) and HOBT (137 mg, 0.90 mmol) in dimethylformamide (3 ml) was stirred in air at room temperature for 1 h, then 4-isoxazolamine (may be prepared as described in Description 95; 100 mg, 1.189 mmol) was added in one charge. The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with water (30 ml). The solid was filtered and dried in vacuo to obtain crude product, which was purified with Prep-HPLC (Waters, X-Bridge, 5 μm; 30×100 mm; A=0.05% NH3.H2O/water, B: MeCN; v=30 ml/min; 0-7 min, 42%-54%; 7-12 min, 95%; t=8.0 min.) to yield the title compound as a white solid. 34 mg.

Workup

  1. additioncharge
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. filtrationThe solid was filtered
  4. customdried in vacuo
  5. customto obtain crude product, which
  6. customwas purified with Prep-HPLC (Waters, X-Bridge, 5 μm
  7. custom0-7 min, 42%-54%
  8. custom7-12 min, 95%

Sources & evidence

ORD record
ord-d02bee0e53674fd5b0a272d6a2897f82
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08778939B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes