Trifluoroacetic acid → 1-({1-[(6-Methylpyridin-3-yl)carbonyl]azetidin-3-yl}carbonyl)-1,4-diazepane

HRID 1402756Notes

Reaction equation

HRID 1402756 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:13][CH:12]([C:14]([N:16]3[CH2:22][CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]3)=[O:15])[CH2:11]2)=[O:9])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:13][CH:12]([C:14]([N:16]3[CH2:22][CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[O:15])[CH2:11]2)=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 66739625Tert-butyl 4-({1-[(6-methylpyridin-3-yl)carbonyl]azetidin-3-yl]carbonyl)-1,4-diazepane-1-carboxylate

Product 1

HCID 667401031-({1-[(6-Methylpyridin-3-yl)carbonyl]azetidin-3-yl}carbonyl)-1,4-diazepaneYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 4-({1-[(6-methylpyridin-3-yl)carbonyl]azetidin-3-yl}carbonyl)-1,4-diazepane-1-carboxylate (455 mg, 1.13 mmol) in DCM (10 mL) was added TFA (440 μL, 5.65 mmol) and stirred at room temperature for 24 hours. The reaction was re-charged with TFA (0.5 mL, 6.5 mmol) and the reaction stirred for a further 5 hours until consumption of starting materials seen by TLC. Volatiles were removed at reduced pressure and the crude product shaken with Ambersep 900-OH resin in DCM (20 ml) for 2 hours. The resin was removed by filtration and the washings concentrated at reduced pressure to give the title compound (302 mg, 89%).

Workup

  1. stirringthe reaction stirred for a further 5 hours until consumption of starting materials
  2. customVolatiles were removed at reduced pressure
  3. stirringthe crude product shaken with Ambersep 900-OH resin in DCM (20 ml) for 2 hours
  4. customThe resin was removed by filtration
  5. concentrationthe washings concentrated at reduced pressure

Sources & evidence

ORD record
ord-022444c231c349c9a94c8c138194b0c9
Source dataset
uspto-grants-2014_12
Patent number
US08912176B2

Reaction notes

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