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Diisopropylethylamine → Tert-butyl 4-({1-[(6-methylpyridin-3-yl)carbonyl]azetidin-3-yl]carbonyl)-1,4-diazepane-1-carboxylate

HRID 1402755
Notes
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Reaction equation

HRID 1402755 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]([N:7]2[CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9][CH2:8]2)=[O:6])[CH2:2]1.CCN(C(C)C)C(C)C.[CH3:30][C:31]1[N:36]=[CH:35][C:34]([C:37](Cl)=[O:38])=[CH:33][CH:32]=1>C(Cl)Cl>[CH3:30][C:31]1[N:36]=[CH:35][C:34]([C:37]([N:1]2[CH2:4][CH:3]([C:5]([N:7]3[CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9][CH2:8]3)=[O:6])[CH2:2]2)=[O:38])=[CH:33][CH:32]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 218904586-Methylnicotinoyl chlorideHCID 66739652Tert-butyl 4-(azetidin-3-ylcarbonyl)-1,4-diazepane-1-carboxylate

Product 1

HCID 66739625Tert-butyl 4-({1-[(6-methylpyridin-3-yl)carbonyl]azetidin-3-yl]carbonyl)-1,4-diazepane-1-carboxylateYield 36.4%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
3×

Procedure

To a stirred solution of tert-butyl 4-(azetidin-3-ylcarbonyl)-1,4-diazepane-1-carboxylate (1.02 g, 3.6 mmol) and DIPEA (1.41 g, 10.8 mmol) in DCM (20 mL) was added a solution of 6-methylpyridine-3-carbonyl chloride (420 mg, 4.32 mmol) in DCM (5 mL) at 0° C. After 3 hours the reaction was diluted with DCM (10 mL), washed with saturated aqueous NaHCO3 (10 mL), brine (5 mL), dried (MgSO4), filtered and concentrated at reduced pressure. Purification by silica FCC (eluting with 100:0:0 to 95:4.5:0.5 gradient of DCM/MeOH/NH3) gave the title compound (527 mg, 36%) as an orange-brown oil.

Workup

  1. washwashed with saturated aqueous NaHCO3 (10 mL), brine (5 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated at reduced pressure
  5. customPurification
  6. washby silica FCC (eluting with 100:0:0 to 95:4.5:0.5 gradient of DCM/MeOH/NH3)

Sources & evidence

ORD record
ord-0d8891ce1c9244c98d578357879f29ec
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08912176B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes