Acetyl chloride → US9777003, Example 216

HRID 628439Notes

Reaction equation

HRID 628439 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[C:14]([NH:21][CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[C:15]3[N:16]([C:17]([CH3:20])=[N:18][N:19]=3)[C:11]=2[CH:10]=[C:9]1[CH3:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29](Cl)(=[O:31])[CH3:30].C(N(CC)CC)C>C(Cl)Cl>[C:29]([N:25]1[CH2:26][CH2:27][CH:22]([NH:21][C:14]2[C:15]3[N:16]([C:17]([CH3:20])=[N:18][N:19]=3)[C:11]3[CH:10]=[C:9]([CH3:28])[N:8]([CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[C:12]=3[CH:13]=2)[CH2:23][CH2:24]1)(=[O:31])[CH3:30]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 118159668US9777003, Example 206

Product 1

HCID 118159618US9777003, Example 216

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 6-benzyl-1,7-dimethyl-N-piperidin-4-yl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridin-4-amine (10. mg, 0.027 mmol, from Example 206) in DCM (1.0 mL) was added acetyl chloride (2.3 μL, 0.032 mmol, Aldrich), followed by the addition of triethylamine (7.4 μL, 0.053 mmol). After 15 minutes, volatiles were removed in vacuo. The mixture was diluted with water and MeOH, and the product was isolated via preparative HPLC-MS (Waters XBridge C18, eluting with a gradient of MeCN/H2O containing 0.15% NH4OH). Yield: (7.6 mg, 68%).

Workup

  1. customvolatiles were removed in vacuo
  2. additionThe mixture was diluted with water and MeOH
  3. customthe product was isolated via preparative HPLC-MS (Waters XBridge C18
  4. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH)

Sources & evidence

ORD record
ord-876889c771f54687b1a2cd3887afca4f
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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