Perchloric Acid → HCID 71209231, compound

HRID 1912553Notes

Reaction equation

HRID 1912553 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[C:16]([CH:17]([OH:22])[C:18]([O:20][CH3:21])=[O:19])=[C:15]([CH3:23])[N:14]=[C:13]4[N:24]([CH2:27][C:28]5[CH:33]=[CH:32][C:31]([F:34])=[C:30]([F:35])[CH:29]=5)[CH:25]=[CH:26][C:12]=34)=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.Cl(O)(=O)(=O)=O>C(OC(C)(C)C)(=O)C>[C:5]([O:22][CH:17]([C:16]1[C:11]([C:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[O:1][CH2:2][CH2:3][CH2:4]3)=[C:12]2[CH:26]=[CH:25][N:24]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([F:34])=[C:30]([F:35])[CH:29]=3)[C:13]2=[N:14][C:15]=1[CH3:23])[C:18]([O:20][CH3:21])=[O:19])([CH3:10])([CH3:6])[CH3:4]

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 71209473HCID 71209473, compound

Product 1

HCID 71209231HCID 71209231, compound

Reagents, catalysts & solvents 1

HCID 10908tert-Butyl acetateSolvent

Procedure

A mixture of methyl 2-(4-(chroman-6-yl)-1-(3,4-difluorobenzyl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-hydroxyacetate (784 mg, 1.638 mmol) in t-Butyl acetate (36 mL) was treated with perchloric acid (0.394 mL, 6.55 mmol) and then stirred at ambient temperature for 40 minutes. The mixture was quenched by adding 15% NaOH and then stirred for 10 minutes. The mixture was extracted with ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate, filtered and concentrated to afford a pale yellow residue: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.30 (dd, J=2.0, 8.4 Hz, 1 H), 7.23-7.06 (m, 3 H), 7.06-6.95 (m, 2 H), 6.90 (dd, J=5.3, 8.4 Hz, 1 H), 6.20 (dd, J=3.5, 10.0 Hz, 1 H), 5.52-5.34 (m, 3 H), 4.28 (t, J=5.2 Hz, 2 H), 3.76 (d, J=5.5 Hz, 3 H), 2.93-2.74 (m, 2 H), 2.71 (d, J=2.7 Hz, 3 H), 2.15-1.96 (m, 2 H), 0.94 (d, J=2.1 Hz, 9 H); LC/MS (m/z) ES+=535 (M+1).

Workup

  1. customThe mixture was quenched
  2. additionby adding 15% NaOH
  3. stirringstirred for 10 minutes
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford a pale yellow residue

Sources & evidence

ORD record
ord-2213dedefe1f40deb8c769683af99065
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

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