Acetonitrile--water (1/1) → HCID 72195160, compound

HRID 879312Notes

Reaction equation

HRID 879312 reaction equation
[C:1]([O:5][C@@H:6]([C:9]1[C:27]([CH3:28])=[CH:26][C:12]2[N:13]=[C:14]([C:16]3[CH:17]=[C:18]4[CH:24]=[N:23][N:22]([CH3:25])[C:19]4=[N:20][CH:21]=3)[S:15][C:11]=2[C:10]=1[C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)[CH2:7][OH:8])([CH3:4])([CH3:3])[CH3:2].[OH2:36].C(#N)C>C(#N)C>[C:1]([O:5][C@@H:6]([C:9]1[C:27]([CH3:28])=[CH:26][C:12]2[N:13]=[C:14]([C:16]3[CH:17]=[C:18]4[CH:24]=[N:23][N:22]([CH3:25])[C:19]4=[N:20][CH:21]=3)[S:15][C:11]=2[C:10]=1[C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)[C:7]([OH:36])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 18373917Acetonitrile--water (1/1)HCID 86699831HCID 86699831, compound

Product 1

HCID 72195160HCID 72195160, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)benzo[d]thiazol-6-yl)ethanol from previous reaction (assume 0.024 mmol) in 25% water/acetonitrile (0.70 mL) was added sequentially, a stock solution of CrO3/H5IO6 (296 μL, 0.439 M solution) and CrO3 (3 mg, 0.030 mmol) at room temperature. The reaction was stirred for 1 h, diluted with acetonitrile, filtered and purified by reverse phase HPLC. Fractions containing product were pooled and evaporated to the desired product. LCMS-ESI+: calc'd for C27H26ClN4O3S: 521.1 (M+H+); 521.2 (M+H+); 1H NMR (400 MHz, CD3OD): δ 9.26 (d, J=1.9 Hz, 1H), 8.79 (d, J=1.9 Hz, 1H), 8.20 (s, 1H), 7.87 (s, 1H), 7.69 (d, J=9.4 Hz, 1H), 7.61-7.59 (m, 3H), 5.26 (s, 1H), 4.15 (s, 3H), 2.61 (s, 3H), 0.97 (s, 9H).

Workup

  1. additionwas added sequentially
  2. customat room temperature
  3. filtrationfiltered
  4. custompurified by reverse phase HPLC
  5. additionFractions containing product
  6. customevaporated to the desired product

Sources & evidence

ORD record
ord-ad216de4718a4e5abfefd81b2b76f028
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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