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Diisopropylethylamine → 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-((3,3-diethyl-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)methyl)-2-methylbenzamide

HRID 1037024
Notes
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Reaction equation

HRID 1037024 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:27])([F:26])[F:25])[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[NH2:62][CH2:63][C:64]1[CH:65]=[CH:66][C:67]2[C:71]([CH2:74][CH3:75])([CH2:72][CH3:73])[O:70][B:69]([OH:76])[C:68]=2[CH:77]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:26])([F:25])[F:27])[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH:62][CH2:63][C:64]4[CH:65]=[CH:66][C:67]5[C:71]([CH2:72][CH3:73])([CH2:74][CH3:75])[O:70][B:69]([OH:76])[C:68]=5[CH:77]=4)=[O:20])=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 231598114-(5-(3,5-Dichlorophenyl)-5-(tri fluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acidHCID 866854706-(aminomethyl)-3,3-diethylbenzo[c][1,2]oxaborol-1(3H)-ol hydrochloride

Product 1

HCID 71576073
4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-((3,3-diethyl-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)methyl)-2-methylbenzamide
Yield 79.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid (100 mg, 0.24 mmol) and DIPEA (151 mg, 1.17 mmol) in DMF (5.0 mL) was stirred at rt for 5 min and then HATU (180 mg, 0.47 mmol) was added. The mixture was stirred for 10 min prior to the addition of 6-(aminomethyl)-3,3-diethylbenzo[c][1,2]oxaborol-1(3H)-ol hydrochloride (63 mg, 0.25 mmol). And the resulting mixture was stirred at rt overnight. It was then concentrated under vacuum, and the residue was partitioned between 1N HCl and ethyl acetate. The organic layer separated was concentrated under vacuum, and the residue was purified by column chromatography and prep-HPLC to provide the final title compound (118 mg, yield 79%). 1H NMR (400 MHz, DMSO-d6): δ 9.00 (s, 1H), 8.88 (t, 1H), 7.80 (t, 1H), 7.60 (m, 5H), 7.42 (d, 1H), 7.40 (d, 1H), 7.24 (d, 1H), 4.47 (d, 2H), 4.36 (d, 2H), 4.27 (d, 2H), 2.35 (s, 3H), 1.78 (m, 4H), 0.52 (t, 6H) ppm; HPLC purity: 92.43% at 220 nm and 93.69% at 254 nm; MS: m/z=620; 661 [M+CH3CN].

Workup

  1. stirringAnd the resulting mixture was stirred at rt overnight
  2. concentrationIt was then concentrated under vacuum
  3. customthe residue was partitioned between 1N HCl and ethyl acetate
  4. customThe organic layer separated
  5. concentrationwas concentrated under vacuum
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-87f7a092a17749d5aeab303ea1fe22c5
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08546357B2

Reaction notes

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