Sodium triacetoxyborohydride → HCID 90013583, compound

HRID 2279146Notes

Reaction equation

HRID 2279146 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[C:15]3[N:17]([CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)[N:18]=[C:19]([CH3:20])[C:14]3=[C:13]([CH2:27][N:28]3[CH2:33][C:32]([CH3:35])([CH3:34])[NH:31][CH2:30][C:29]3([CH3:37])[CH3:36])[CH:12]=2)=[CH:7][CH:6]=1.[C:38]([N:45]([CH2:47][CH:48]=O)[CH3:46])([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(OCC)(=O)C.O>[C:41]([O:40][C:38](=[O:39])[N:45]([CH2:47][CH2:48][N:31]1[CH2:30][C:29]([CH3:37])([CH3:36])[N:28]([CH2:27][C:13]2[CH:12]=[C:11]([C:8]3[CH:7]=[CH:6][C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:10][CH:9]=3)[N:16]=[C:15]3[N:17]([CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)[N:18]=[C:19]([CH3:20])[C:14]=23)[CH2:33][C:32]1([CH3:35])[CH3:34])[CH3:46])([CH3:44])([CH3:43])[CH3:42]

Participants

7

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 10725881tert-butyl N-methyl-N-(2-oxoethyl)carbamateHCID 90013940HCID 90013940, compound

Product 1

HCID 90013583HCID 90013583, compoundYield 404.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 290 mg of 6-(4-methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-4-(2,2,5,5-tetramethyl-piperazin-1-ylmethyl)-1H-pyrazolo[3,4-b]pyridine and 1040 mg N-Boc-(methylamino)acetaldehyde in 5 ml dichloromethane was added 250 mg of sodium triacetoxyborohydride. After 1 h at rt the reaction was diluted with ethyl acetate and water. The phases were separated. The aqueous phase was extracted with ethyl acetate twice. The combined organic phases were dried over sodium sulphate, filtrated and concentrated in vacuo. 1535 mg of a crude product of the title compound were obtained, which was used without purification in the next step.

Workup

  1. customThe phases were separated
  2. extractionThe aqueous phase was extracted with ethyl acetate twice
  3. dry with materialThe combined organic phases were dried over sodium sulphate
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ef51eaacc42d4ba6ac0ae115aee92de8
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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