Acetonitrile → N-Cyclopropylmethyl-2-methyl-N'-(5-methyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin 7-yl)-malonamide

HRID 1372932Notes

Reaction equation

HRID 1372932 reaction equation
[CH3:1][CH:2]([C:6]([NH:8][CH:9]1[C:15](=[O:16])[N:14]([CH3:17])[C:13]2[CH:18]=[CH:19][CH:20]=[CH:21][C:12]=2[C:11]2[CH:22]=[CH:23][CH:24]=[CH:25][C:10]1=2)=[O:7])[C:3](O)=[O:4].[CH:26]1([CH2:29][NH2:30])[CH2:28][CH2:27]1.[B-](F)(F)(F)F.CN(C(ON1C(=O)C=CC=C1)=[N+](C)C)C.CC#N>CN(C=O)C.C(O)(C(F)(F)F)=O>[CH:26]1([CH2:29][NH:30][C:3](=[O:4])[CH:2]([CH3:1])[C:6]([NH:8][CH:9]2[C:15](=[O:16])[N:14]([CH3:17])[C:13]3[CH:18]=[CH:19][CH:20]=[CH:21][C:12]=3[C:11]3[CH:22]=[CH:23][CH:24]=[CH:25][C:10]2=3)=[O:7])[CH2:28][CH2:27]1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 75646CyclopropanemethanamineHCID 2733204O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium TetrafluoroborateHCID 210725002-Methyl-N-(5-methyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-malonamic acid

Product 1

HCID 11257831N-Cyclopropylmethyl-2-methyl-N'-(5-methyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin 7-yl)-malonamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

2-Methyl-N-(5-methyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-malonamic acid (20 mg, 0.059 mmol) and cyclopropylmethylamine (5 mg, 0.059 mmol) were placed in a disposable polypropylene tube and dissolved in DMF (2 ml). TPTU (2-(2-pyridon-1-yl)-1,1,3,3-tetramethyl uronium tetrafluoroborate, 19 mg, 0.065 mmol) was added, and the mixture was shaken overnight at r.t. The title compound, MS: m/e=392.2 (M+H+), was isolated from the reaction mixture by automated, preparative HPLC (YMC CombiPrep C18 column 50×20 mm, solvent gradient 5–95% CH3CN in 0.1% TFA(aq) over 6.0 min, λ=230 nm, flow rate 40 ml/min).

Sources & evidence

ORD record
ord-c27a21c525da447a851c58ee45f9945c
Source dataset
uspto-grants-2007_01
Patent number
US07160875B2

Reaction notes

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