Trifluoroacetic acid → HCID 67252221, compound

HRID 1798203Notes

Reaction equation

HRID 1798203 reaction equation
COC1C=CC(OC)=CC=1C[NH:6][C:7]1[N:12]=[C:11]([O:13][C:14]2[CH:15]=[C:16]([CH3:28])[C:17]3[CH:21]([CH2:22][C:23]([OH:25])=[O:24])[O:20][B:19]([OH:26])[C:18]=3[CH:27]=2)[CH:10]=[CH:9][N:8]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:23]([OH:25])=[O:24].[NH2:6][C:7]1[N:12]=[C:11]([O:13][C:14]2[CH:15]=[C:16]([CH3:28])[C:17]3[CH:21]([CH2:22][C:23]([OH:25])=[O:24])[O:20][B:19]([OH:26])[C:18]=3[CH:27]=2)[CH:10]=[CH:9][N:8]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 67254018HCID 67254018, compound

Product 1

HCID 67252221HCID 67252221, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of {6-[2-(2,5-dimethoxy-benzylamino)-pyrimidin-4-yloxy]-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl}-acetic acid (0.32 g, 0.69 mmol) in CH2Cl2 (10 mL) was treated with trifluoroacetic acid (1 mL, 12.98 mmol) and refluxed for 18 hours. A second portion of trifluoroacetic acid was added (1 mL, 12.98 mmol) and the solution was refluxed for another 18 hours. The mixture was concentrated and purified by preparative HPLC (CH3CN/0.1% formic acid in water) to give [6-(2-amino-pyrimidin-4-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid formic acid salt as a white solid (0.10 g, 46%) after lyophilization. 1H NMR (400 MHz, DMSO-d δ9.26 (br s, 1H), 8.14 (d, J=6.24 Hz, 1H), 8.11 (s, 1H), 7.24 (d, J=2.34 Hz, 1H), 7.17 (br s, 2H), 7.08 (d, J=2.34 Hz, 1H), 6.26 (d, J=5.86 Hz, 1H), 5.51 (dd, J=9.76, 2.73 Hz, 1H), 3.08 (dd, J=15.61, 2.73 Hz, 1H), 2.29 (d, 3H), 2.10 (dd, J=15.76, 9.76 Hz, 1H). MS (ESI) m/z: 316 [M+1].

Workup

  1. temperaturerefluxed for 18 hours
  2. temperaturethe solution was refluxed for another 18 hours
  3. concentrationThe mixture was concentrated
  4. custompurified by preparative HPLC (CH3CN/0.1% formic acid in water)

Sources & evidence

ORD record
ord-72e86389195149f4ad7611f6dbee868a
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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