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1-Hydroxybenzotriazole → 1-Cyclobutyl-4-({1-[(4-methoxycyclohexyl)carbonyl]azetidin-3-yl}carbonyl)-1,4-diazepane

HRID 1402736
Notes
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Reaction equation

HRID 1402736 reaction equation
[CH3:1][O:2][CH:3]1[CH2:8][CH2:7][CH:6]([C:9]([OH:11])=O)[CH2:5][CH2:4]1.C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:46]1[CH2:49][CH:48]([C:50]([N:52]2[CH2:58][CH2:57][CH2:56][N:55]([CH:59]3[CH2:62][CH2:61][CH2:60]3)[CH2:54][CH2:53]2)=[O:51])[CH2:47]1>CN(C=O)C.C(Cl)Cl.C(Cl)Cl>[CH:59]1([N:55]2[CH2:56][CH2:57][CH2:58][N:52]([C:50]([CH:48]3[CH2:47][N:46]([C:9]([CH:6]4[CH2:5][CH2:4][CH:3]([O:2][CH3:1])[CH2:8][CH2:7]4)=[O:11])[CH2:49]3)=[O:51])[CH2:53][CH2:54]2)[CH2:62][CH2:61][CH2:60]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 736153Rac-(1r,4r)-4-methoxycyclohexane-1-carboxylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 667393581-(Azetidin-3-ylcarbonyl)-4-cyclobutyl-1,4-diazepane

Product 1

HCID 46851657
1-Cyclobutyl-4-({1-[(4-methoxycyclohexyl)carbonyl]azetidin-3-yl}carbonyl)-1,4-diazepane
Yield 11%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To a stirred solution of 4-methoxycyclohexane carboxylic acid (20 mg, 0.13 mmol) in DMF/DCM (1:1) (2 ml) was added HOBt (38 mg, 0.28 mmol) and HBTU (96 mg, 0.25 mmol) and the reaction mixture stirred for 15 mins at RT. 1-(Azetidin-3-ylcarbonyl)-4-cyclobutyl-1,4-diazepane (30 mg, 0.13 mmol) in DCM (1 ml) was added and the reaction mixture stirred at RT for 16 hrs. Upon completion, the reaction mixture was evaporated at reduced pressure and purified by silica gel FCC (using DCM/MeOH/NH3; 95:5:0.5 to 90:10:1 as eluent) to give the title compound as colourless oil and as a 1:1 mixture of diastereoisomers by 1H NMR spectroscopy (5.2 mg, 11% yield).

Workup

  1. stirringthe reaction mixture stirred at RT for 16 hrs
  2. customUpon completion, the reaction mixture was evaporated at reduced pressure
  3. custompurified by silica gel FCC (using DCM/MeOH/NH3; 95:5:0.5 to 90:10:1 as eluent)

Sources & evidence

ORD record
ord-7f6a13ac809341bcacbd30d56d8f8001
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