Diisopropylethylamine → HCID 71575728, compound

HRID 1037104Notes

Reaction equation

HRID 1037104 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:27]([F:30])([F:29])[F:28])[O:14][N:13]=[C:12]([C:15]3[N:16]4[C:20]([C:21]([C:24]([OH:26])=O)=[CH:22][CH:23]=3)=[CH:19][CH:18]=[CH:17]4)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8].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.[NH2:65][CH2:66][C:67]1[CH:68]=[CH:69][C:70]2[C:74]([CH2:77][CH3:78])([CH2:75][CH3:76])[O:73][B:72]([OH:79])[C:71]=2[CH:80]=1>CN(C=O)C>[Cl:9][C:6]1[CH:5]=[C:4]([C:10]2([C:27]([F:30])([F:29])[F:28])[O:14][N:13]=[C:12]([C:15]3[N:16]4[C:20]([C:21]([C:24]([NH:65][CH2:66][C:67]5[CH:68]=[CH:69][C:70]6[C:74]([CH2:75][CH3:76])([CH2:77][CH3:78])[O:73][B:72]([OH:79])[C:71]=6[CH:80]=5)=[O:26])=[CH:22][CH:23]=3)=[CH:19][CH:18]=[CH:17]4)[CH2:11]2)[CH:3]=[C:2]([Cl:1])[C:7]=1[F:8]

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 866854706-(aminomethyl)-3,3-diethylbenzo[c][1,2]oxaborol-1(3H)-ol hydrochlorideHCID 866855275-(5-(3,5-Dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)indolizine-8-carboxylic acid

Product 1

HCID 71575728HCID 71575728, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)indolizine-8-carboxylic acid (0.23 mmol) and DIPEA (118 mg, 0.92 mmol) in DMF (5 mL) can be stirred at rt for 5 min and then HATU (175 mg, 0.46 mmol) can be added. The mixture can be stirred for 10 min prior to the addition of 6-(aminomethyl)-3,3-diethylbenzo[c][1,2]-oxaborol-1(3H)-ol hydrochloride (118 mg, 0.46 mmol). And the resulting mixture can be stirred at rt overnight. It can be then concentrated under vacuum, and the residue can be partitioned between 1N HCl and ethyl acetate. The organic layer separated can be concentrated under vacuum, and the residue can be purified on column chromatography and prep-HPLC to provide the title compound.

Workup

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

Sources & evidence

ORD record
ord-878b25a896b341d886d0dbef483ac29c
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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