Diisopropylethylamine → HCID 71575779, compound

HRID 1037110Notes

Reaction equation

HRID 1037110 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:26]([F:29])([F:28])[F:27])[O:13][N:12]=[C:11]([C:14]3[N:15]4[C:19]([C:20]([C:23]([OH:25])=O)=[CH:21][CH:22]=3)=[CH:18][CH:17]=[CH:16]4)[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.[NH2:64][CH2:65][C:66]1[CH:67]=[CH:68][C:69]2[C:73]([CH2:76][F:77])([CH2:74][F:75])[O:72][B:71]([OH:78])[C:70]=2[CH:79]=1>CN(C=O)C>[F:77][CH2:76][C:73]1([CH2:74][F:75])[O:72][B:71]([OH:78])[C:70]2[CH:79]=[C:66]([CH2:65][NH:64][C:23]([C:20]3[C:19]4[N:15]([CH:16]=[CH:17][CH:18]=4)[C:14]([C:11]4[CH2:10][C:9]([C:4]5[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=5)([C:26]([F:29])([F:27])[F:28])[O:13][N:12]=4)=[CH:22][CH:21]=3)=[O:25])[CH:67]=[CH:68][C:69]1=2

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 67247370HCID 67247370, compoundHCID 866854756-(aminomethyl)-3,3-bis(fluoromethyl)benzo[c][1,2]oxaborol-1(3H)-ol hydrochloride

Product 1

HCID 71575779HCID 71575779, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)indolizine-8-carboxylic acid (0.24 mmol) and DIPEA (124 mg, 0.88 mmol) in DMF (5 mL) can be stirred at rt for 5 min and then HATU (183 mg, 0.48 mmol) can be added. The mixture can be stirred for 10 min prior to the addition of 6-(aminomethyl)-3,3-bis(fluoromethyl)benzo[c][1,2]oxaborol-1(3H)-ol hydrochloride (126 mg, 0.44 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 by prep-TLC to provide the final title product.

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 by prep-TLC

Sources & evidence

ORD record
ord-6a02ce9117ab4d3f97d98d9ba20166d1
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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