Triethylamine → HCID 67275267, compound

HRID 1696898Notes

Reaction equation

HRID 1696898 reaction equation
Cl[C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:21])[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:8][N:9]2[CH2:12][CH2:13][C:14]#[N:15])=[CH:4][C:3]=1[F:22].Cl.[NH:24]1[CH2:27][CH2:26][CH2:25]1.C(N(CC)CC)C>ClCCl>[N:24]1([C:2]2[N:11]=[C:10]3[C:5]([C:6](=[O:21])[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:8][N:9]3[CH2:12][CH2:13][C:14]#[N:15])=[CH:4][C:3]=2[F:22])[CH2:27][CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 12308726Azetidine hydrochlorideHCID 87333591HCID 87333591, compound

Product 1

HCID 67275267HCID 67275267, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of Example 7C (13.26 g), azetidine hydrochloride (9.58 g) and triethylamine (17.2 mL) in dichloromethane (650 mL) was stirred for 2 hours, treated with triethylamine (900 mg), stirred for 1 hour, diluted with dichloromethane, washed with water and brine, dried (MgSO4), filtered, and concentrated; and the concentrate was triturated with refluxing dichloromethane, treated with diethyl ether and hexanes, and filtered.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customand the concentrate was triturated with refluxing dichloromethane
  6. additiontreated with diethyl ether and hexanes
  7. filtrationfiltered

Sources & evidence

ORD record
ord-909207a3824943d3ae3049444ceac784
Source dataset
uspto-grants-2012_04
Patent number
US08163769B2

Reaction notes

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