Azetidine → HCID 118159937, compound

HRID 628401Notes

Reaction equation

HRID 628401 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([CH2:14][N:15]2[C:19]3[CH:20]=[CH:21][C:22]4[N:23]([C:24]([CH3:27])=[N:25][N:26]=4)[C:18]=3[CH:17]=[C:16]2[C:28]2[O:29][CH:30]=[N:31][N:32]=2)[CH:13]=1)[CH2:5][N:6]1[CH2:9][CH:8](O)[CH2:7]1.N1CCC1>C1COCC1>[N:6]1([CH2:5][C:4]2[CH:11]=[C:12]([CH:13]=[C:2]([Cl:1])[CH:3]=2)[CH2:14][N:15]2[C:19]3[CH:20]=[CH:21][C:22]4[N:23]([C:24]([CH3:27])=[N:25][N:26]=4)[C:18]=3[CH:17]=[C:16]2[C:28]2[O:29][CH:30]=[N:31][N:32]=2)[CH2:7][CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 10422Azetidine2×HCID 118159936HCID 118159936, compound

Product 1

HCID 118159937HCID 118159937, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The remaining mesylate solution prepared in Example 139, Step 5 was treated with the solution of azetidine (0.023 mL, 0.33 mmol, Aldrich) in THF (0.2 mL). After 20 minutes, additional azetidine (0.078 mL, 1.1 mmol, Aldrich) was added and the reaction was stirred overnight. The product was isolated by preparative HPLC-MS (Waters XBridge C18, eluting with a gradient of MeCN/H2O containing 0.15% NH4OH). Yield: (5 mg, 10%).

Workup

  1. customThe product was isolated by preparative HPLC-MS (Waters XBridge C18
  2. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH)

Sources & evidence

ORD record
ord-3d0a118336df4d9394407b225153569b
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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