Acetyl chloride → HCID 86677761, compound

HRID 1499838Notes

Reaction equation

HRID 1499838 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl:5][C:6]1[C:7]([CH3:38])=[C:8]([C:27]2[CH:28]=[N:29][N:30]([CH:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[CH:31]=2)[C:9]([O:25][CH3:26])=[C:10]([CH:12]([N:14]2[C:18]3=[N:19][CH:20]=[N:21][C:22]([NH2:23])=[C:17]3[C:16]([CH3:24])=[N:15]2)[CH3:13])[CH:11]=1.C(N(C(C)C)CC)(C)C.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[C:1]([N:35]1[CH2:34][CH2:33][CH:32]([N:30]2[CH:31]=[C:27]([C:8]3[C:9]([O:25][CH3:26])=[C:10]([CH:12]([N:14]4[C:18]5=[N:19][CH:20]=[N:21][C:22]([NH2:23])=[C:17]5[C:16]([CH3:24])=[N:15]4)[CH3:13])[CH:11]=[C:6]([Cl:5])[C:7]=3[CH3:38])[CH:28]=[N:29]2)[CH2:37][CH2:36]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 19871184HCID 19871184, compoundHCID 86677759HCID 86677759, compound2×

Product 1

HCID 86677761HCID 86677761, compoundYield 11.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (2.4 μL, 0.033 mmol) was added to a solution of 1-{1-[5-chloro-2-methoxy-4-methyl-3-(1-piperidin-4-yl-1H-pyrazol-4-yl)phenyl]ethyl}-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (8.0 mg, 0.017 mmol, chiral intermediate from Example 181, Step 2) and N,N-diisopropylethylamine diisopropylethylamine (14 μL, 0.083 mmol) in methylene chloride (0.3 mL) at 0° C. and the reaction was stirred at room temperature for 15 min. The crude 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 (1.0 mg, 7.8%). The product was isolated as a single enantiomer. LCMS calculated for C26H32ClN8O2 (M+H)+: m/z=523.2; Found: 523.2.

Workup

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

Sources & evidence

ORD record
ord-c5a6d08551274cdda60cdae1a411a845
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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