HCID 67492526, compound → HCID 59605854, compound

HRID 1923380Notes

Reaction equation

HRID 1923380 reaction equation
[CH2:1]([C:3]1[N:7]([C:8]2[N:16]=[C:15]3[C:11]([N:12]=[C:13]([C:18]4([O:26][CH3:27])[CH2:21][N:20]([C:22](=O)[CH2:23][OH:24])[CH2:19]4)[N:14]3[CH3:17])=[C:10]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[N:9]=2)[C:6]2[CH:34]=[CH:35][CH:36]=[CH:37][C:5]=2[N:4]=1)[CH3:2]>C1COCC1>[CH2:1]([C:3]1[N:7]([C:8]2[N:16]=[C:15]3[C:11]([N:12]=[C:13]([C:18]4([O:26][CH3:27])[CH2:19][N:20]([CH2:22][CH2:23][OH:24])[CH2:21]4)[N:14]3[CH3:17])=[C:10]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[N:9]=2)[C:6]2[CH:34]=[CH:35][CH:36]=[CH:37][C:5]=2[N:4]=1)[CH3:2]

Participants

3

Reactant 1

HCID 67492526HCID 67492526, compound

Product 1

HCID 59605854HCID 59605854, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-{3-[2-(2-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purin-8-yl]-3-methoxyazetidin-1-yl}-2-hydroxyethanone (88 mg, 0.17 mmol) in THF (2 mL) at 0° C. was added BH3.THF complex (350 μL, 0.35 mmol, 1M solution) and the resulting mixture allowed to stir for 1 h. Further BH3.THF complex (800 μL, 0.80 mmol) was added and the mixture stirred at r.t. for 17 h. The reaction mixture was quenched with H2O, acidified with 2M HCl then loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH. The resulting residue was dissolved in a mixture of MeCN and H2O and allowed to freeze-dry affording 849 as a white solid (74 mg, 86%). LCMS (method I): RT 2.48 min, [M+H]+ 493.4. 1H NMR (DMSO, 400 MHz): δ 8.04-8.04 (1 H, m), 7.64-7.63 (1 H, m), 7.27-7.23 (2 H, m), 4.50-4.42 (1 H, m), 4.39-4.14 (4 H, brd m), 4.05-3.98 (2 H, m), 3.80 (4 H, t, J=4.56 Hz), 3.70 (3 H, s), 3.52-3.45 (2 H, m), 3.40 (2 H, q, J=5.63 Hz), 3.34-3.24 (2 H, m), 3.01 (3 H, s), 2.65-2.57 (2 H, m), 1.34 (3 H, t, J=7.43 Hz)

Workup

  1. additionFurther BH3.THF complex (800 μL, 0.80 mmol) was added
  2. stirringthe mixture stirred at r.t. for 17 h
  3. customThe reaction mixture was quenched with H2O
  4. washwas washed with MeOH
  5. washthe product eluted with 2M NH3/MeOH
  6. dissolutionThe resulting residue was dissolved in a mixture of MeCN and H2O
  7. customto freeze-dry

Sources & evidence

ORD record
ord-56f978a7d6e34f9888f100672d400c39
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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