Acetone → HCID 86677845, compound

HRID 1499928Notes

Reaction equation

HRID 1499928 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:12]([C:14]3[CH:21]=[C:20]([CH3:22])[C:17]([C:18]#[N:19])=[C:16]([CH:23]4[CH2:26][NH:25][CH2:24]4)[C:15]=3[O:27][CH2:28][CH3:29])[CH3:13])[N:9]=[C:10]([CH3:11])[C:3]=12.[CH3:30][C:31]([CH3:33])=O.C([BH3-])#N.[Na+]>CO>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:12]([C:14]3[CH:21]=[C:20]([CH3:22])[C:17]([C:18]#[N:19])=[C:16]([CH:23]4[CH2:26][N:25]([CH:31]([CH3:33])[CH3:30])[CH2:24]4)[C:15]=3[O:27][CH2:28][CH3:29])[CH3:13])[N:9]=[C:10]([CH3:11])[C:3]=12

Participants

5

Reactant 3

HCID 180AcetoneHCID 5003444Sodium cyanoborohydrideHCID 86677846HCID 86677846, compound

Product 1

HCID 86677845HCID 86677845, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 4-[1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-2-azetidin-3-yl-3-ethoxy-6-methylbenzonitrile (70 mg, 0.2 mmol) in methanol (50 mL) was added acetone (0.1 mL, 2 mmol) and sodium cyanoborohydride (17 mg, 0.27 mmol). The reaction was stirred at room temperature for 1 h, and was complete by LC/MS. The reaction was quenched with water and was extracted with EtOAc. The combined organic layer was washed with brine, dried over MgSO4, filtered and concentrated to give the crude product. The product was purified by prep HPLC on a C-18 column eluting water:acetonitrile gradient buffered pH 10 to give the title compound as a white amorphous solid (0.030 g, 40%). The product was isolated as a racemic mixture. LCMS calculated for C24H32N7O(M+H)+: m/z=434.2; found: 434.3. 1H NMR (300 MHz, CD3OD) δ 8.17 (s, 1H), 7.35 (s, 1H), 6.37 (q, J=7.1 Hz, 1H), 4.17-3.98 (m, 4H), 3.90-3.71 (m, 3H), 2.65 (s, 3H), 2.46 (s, 4H), 1.84 (d, J=7.1 Hz, 3H), 1.42 (t, J=7.0 Hz, 3H), 1.03 (dd, J=6.2, 1.4 Hz, 6H).

Workup

  1. customThe reaction was quenched with water
  2. extractionwas extracted with EtOAc
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product
  8. customThe product was purified by prep HPLC on a C-18 column
  9. washeluting water

Sources & evidence

ORD record
ord-39dc221aa48f49c9a575d02371cd0d60
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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