Acetyl chloride → HCID 86677724, compound

HRID 1499799Notes

Reaction equation

HRID 1499799 reaction equation
Cl.Cl.[NH2:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]2[N:10]([CH:16]([C:18]3[C:19]([O:31][CH3:32])=[C:20]([CH:27]4[CH2:30][NH:29][CH2:28]4)[C:21]([CH3:26])=[C:22]([CH:25]=3)[C:23]#[N:24])[CH3:17])[N:11]=[C:12]([CH:13]([F:15])[F:14])[C:5]=12.[C:33](Cl)(=[O:35])[CH3:34].C(N(CC)CC)C>C(Cl)Cl>[C:33]([N:29]1[CH2:30][CH:27]([C:20]2[C:21]([CH3:26])=[C:22]([CH:25]=[C:18]([CH:16]([N:10]3[C:6]4=[N:7][CH:8]=[N:9][C:4]([NH2:3])=[C:5]4[C:12]([CH:13]([F:14])[F:15])=[N:11]3)[CH3:17])[C:19]=2[O:31][CH3:32])[C:23]#[N:24])[CH2:28]1)(=[O:35])[CH3:34]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86677719HCID 86677719, compound2×

Product 1

HCID 86677724HCID 86677724, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-{1-[4-amino-3-(difluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl}-3-azetidin-3-yl-4-methoxy-2-methylbenzonitrile dihydrochloride (21 mg, 0.043 mmol, racemic intermediate from Example 129, Step 2), acetyl chloride (3.4 μL, 0.048 mmol), and triethylamine (18 μL, 0.13 mmol) in methylene chloride (0.3 mL) was stirred overnight at room temperature. The solvents were evaporated and the crude material was purified using RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min) to give the desired product. The product was isolated as a racemic mixture. LCMS calculated for C22H24F2N7O2 (M+H)+: m/z=456.2; Found: 456.2.

Workup

  1. customThe solvents were evaporated
  2. customthe crude material was purified
  3. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min)

Sources & evidence

ORD record
ord-6a0110f3da6448d8a1cd7ca0cd984804
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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