Cyclopentylamine → HCID 67236497, compound

HRID 1521768Notes

Reaction equation

HRID 1521768 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]([C:10]2[CH:11]=[CH:12][C:13]3[CH:14]=[C:15]4[C:21](=[O:22])[NH:20][CH2:19][CH2:18][CH2:17][N:16]4[C:23]=3[N:24]=2)=[O:9])[N:4]=[C:3]1[C:25](O)=[O:26].[CH:28]1([NH2:33])[CH2:32][CH2:31][CH2:30][CH2:29]1.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C.CN(C1C=CN=CC=1)C.O>[CH:28]1([NH:33][C:25]([C:3]2[N:2]([CH3:1])[CH:6]=[C:5]([NH:7][C:8]([C:10]3[CH:11]=[CH:12][C:13]4[CH:14]=[C:15]5[C:21](=[O:22])[NH:20][CH2:19][CH2:18][CH2:17][N:16]5[C:23]=4[N:24]=3)=[O:9])[N:4]=2)=[O:26])[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

9

Reactant 5

HCID 2906CyclopentylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67238228HCID 67238228, compound

Product 1

HCID 67236497HCID 67236497, compoundYield 10%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-methyl-4-{[(6-oxo-7,8,9,10-tetrahydro-6H-pyrido[3′,2′:4,5]pyrrolo[1,2-a][1,4]diazepin-2-yl)carbonyl]amino}-1H-imidazole-2-carboxylic acid (50 mg, 0.14 mmol) in DMF (1.5 mL) was added cyclopentylamine (27 μL, 0.27 mmol), HOBt (18 mg, 0.14 mmol), N,N-diisopropylethylamine (47 μL, 0.27 mmol), and DMAP (3 mg, 0.027 mmol) followed by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (78 mg, 0.41 mmol). The mixture is stirred at room temperature for 64 h. The mixture is poured over H2O and the resulting solid is collected by filtration and is purified via preparative HPLC using a gradient elution from 10-75% acetonitrile/H2O with 0.1% TFA to obtain the title compound (6 mg, 10%). LCMS: 436.20 (M+H+). (System V-med polar)

Workup

  1. filtrationthe resulting solid is collected by filtration
  2. customis purified via preparative HPLC
  3. washa gradient elution from 10-75% acetonitrile/H2O with 0.1% TFA

Sources & evidence

ORD record
ord-597b5d0c0dc246bca327b50b5939c980
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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