HCID 53629068, compound → HCID 53629037, compound

HRID 244195Notes

Reaction equation

HRID 244195 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH:27]3[CH2:30][C:29](CO)([OH:31])[CH2:28]3)=[N:9][C:10]=2[C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:18]3)=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1>C1COCC1.O.C(Cl)Cl>[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH:27]3[CH2:28][C:29](=[O:31])[CH2:30]3)=[N:9][C:10]=2[C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:18]3)=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1

Participants

4

Reactant 1

HCID 53629068HCID 53629068, compound

Product 1

HCID 53629037HCID 53629037, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 3-[8-amino-1-(2-phenylquinolin-7-yl)-imidazo[1,5-a]pyrazin-3-yl]-1-hydroxymethyl-cyclobutanol (7.282 g, 17.69 mmol) in THF-water mixture (200 mL, 3:1) was added NaIO4 (4.542 g, 21.23 mmol) and the reaction was stirred at rt overnight. The reaction mixture was diluted with DCM (500 mL) and the DCM layer was separated, washed with brine, dried over anhydrous Na2SO4 and evaporated in vacuo. The crude product was purified by chromatography on silica gel using DCM:MeOH as eluent (0%→2%) yielded the desired compound as a yellow solid. MS (ES+): m/z 406.15 [MH+]. HPLC: tR=2.23 min (OpenLynx, polar—5 min). 1H NMR (400 MHz, CDCl3) δ 3.60-3.36 (m, 2H), 3.82-3.92 (m, 3H), 5.31 (br, 2H), 7.21 (dd, J=12.8, 4.8 Hz, 2H), 7.48-7.56 (m, 3H), 7.91-7.98 (m, 3H), 8.18-8.20 (m, 2H), 8.28 (d, J=8.0 Hz, 1H), 8.42 (s, 1H).

Workup

  1. customthe DCM layer was separated
  2. washwashed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. customevaporated in vacuo
  5. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-4f70794115014064b2db908235d0f3d5
Source dataset
uspto-grants-2014_02
Patent number
US08653268B2

Reaction notes

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