Hydrochloric Acid → HCID 71576473, compound

HRID 1037094Notes

Reaction equation

HRID 1037094 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](O)=[O:24])=[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(CC)CC.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:75]=[CH:74][C:67]2[B:68]([OH:73])[O:69][C:70]([CH3:72])([CH3:71])[C:66]=2[CH:65]=1.Cl>C(#N)C>[Cl:8][C:6]1[CH:5]=[C:4]([C:9]2([C:26]([F:28])([F:27])[F:29])[O:13][N:12]=[C:11]([C:14]3[N:15]4[C:19]([C:20]([C:23]([NH:62][CH2:63][C:64]5[CH:75]=[CH:74][C:67]6[B:68]([OH:73])[O:69][C:70]([CH3:72])([CH3:71])[C:66]=6[CH:65]=5)=[O:24])=[CH:21][CH:22]=3)=[CH:18][CH:17]=[CH:16]4)[CH2:10]2)[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 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 86685451HCID 86685451, compound

Product 1

HCID 71576473HCID 71576473, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)indolizine-8-carboxylic acid (0.72 mmol) in acetonitrile (5 ml) at 0° C. can be added Et3N (291.1 mg, 2.88 mmol), HATU (546.76 mg, 1.44 mmol) and 5-(aminomethyl)-3,3-dimethyl-benzo[c][1,2]oxaborol-1(3H)-ol hydrochloride (194.2 mg, 0.86 mmol). The reaction mixture can be stirred overnight at rt. The mixture can be poured into 1N HCl solution and extracted with EA (20 ml×3). The combined organic layers can be washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue can be purified by prep-TLC and prep-HPLC to give the final title compound.

Workup

  1. extractionextracted with EA (20 ml×3)
  2. washThe combined organic layers can be washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue can be purified by prep-TLC and prep-HPLC

Sources & evidence

ORD record
ord-63c6c7bd5a0042fa916fa166c61d424c
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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