Acetone → HCID 71279114, compound

HRID 1499746Notes

Reaction equation

HRID 1499746 reaction equation
[ClH:1].Cl.[NH:3]1[CH2:6][CH:5]([C:7]2[C:8]([O:28][CH3:29])=[C:9]([CH:15]([N:17]3[C:21]4=[N:22][CH:23]=[N:24][C:25]([NH2:26])=[C:20]4[C:19]([CH3:27])=[N:18]3)[CH3:16])[CH:10]=[C:11](Cl)[C:12]=2[F:13])[CH2:4]1.[CH3:30][C:31]([CH3:33])=O.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[Cl:1][C:7]1([CH:5]2[CH2:6][N:3]([CH:31]([CH3:33])[CH3:30])[CH2:4]2)[C:12]([F:13])=[CH:11][CH:10]=[C:9]([CH:15]([N:17]2[C:21]3=[N:22][CH:23]=[N:24][C:25]([NH2:26])=[C:20]3[C:19]([CH3:27])=[N:18]2)[CH3:16])[CH:8]1[O:28][CH3:29]

Participants

6

Reactant 4

HCID 180AcetoneHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86677675HCID 86677675, compound

Product 1

HCID 71279114HCID 71279114, compoundYield 105.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-[1-(3-azetidin-3-yl-5-chloro-4-fluoro-2-methoxyphenyl)ethyl]-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine dihydrochloride (0.90 g, 1.9 mmol, Example 67, step 1), acetone (1.0 mL, 14 mmol) and triethylamine (2.5 mL, 18 mmol) in methylene chloride (20 mL) was added sodium triacetoxyborohydride resin (2.5 g, 5.8 mmol). The mixture was stirred at room temperature for 2 h, then filtered, washed with water, dried over MgSO4, filtered and concentrated to give crude product (870 mg, 100%). LCMS calculated for C21H27ClFN6O (M+H)+: m/z=433.2; Found: 433.1

Workup

  1. filtrationfiltered
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d374da5ac9834840810265a94f3f5aed
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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