Acetyl chloride → HCID 118159415, compound

HRID 628344Notes

Reaction equation

HRID 628344 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][C:15]3[N:16]([C:17]([CH3:20])=[N:18][N:19]=3)[C:11]=2[CH:10]=[C:9]1[C:21]1[CH:25]=[CH:24][N:23]([C:26]2([CH2:30][C:31]#[N:32])[CH2:29][NH:28][CH2:27]2)[N:22]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:33](Cl)(=[O:35])[CH3:34].C(N(CC)CC)C>C(Cl)Cl>[C:33]([N:28]1[CH2:29][C:26]([CH2:30][C:31]#[N:32])([N:23]2[CH:24]=[CH:25][C:21]([C:9]3[N:8]([CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[C:12]4[CH:13]=[CH:14][C:15]5[N:16]([C:17]([CH3:20])=[N:18][N:19]=5)[C:11]=4[CH:10]=3)=[N:22]2)[CH2:27]1)(=[O:35])[CH3:34]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 118159918HCID 118159918, compound

Product 1

HCID 118159415HCID 118159415, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To {3-[3-(6-benzyl-1-methyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridin-7-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile (8.0 mg, 0.019 mmol, from Example 90) was added acetyl chloride (1.6 μL, 0.022 mmol, Aldrich) in DCM (0.50 mL), followed by triethylamine (5.3 μL, 0.038 mmol). The reaction was complete in 5 minutes. Purification via preparative HPLC-MS (C18 eluting with a gradient of MeCN and H2O containing 0.15% NH4OH) afforded desired product (8.2 mg, 93%).

Workup

  1. customPurification via preparative HPLC-MS (C18
  2. washeluting with a gradient of MeCN and H2O containing 0.15% NH4OH)

Sources & evidence

ORD record
ord-fe82949e576d44a8ac85307a06a665d7
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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