1-Hydroxybenzotriazole → HCID 57928295, compound

HRID 1360194Notes

Reaction equation

HRID 1360194 reaction equation
[O:1]=[C:2]1[N:13]([CH:14]2[CH:21]3[CH2:22][C:17]4([C:24](O)=[O:25])[CH2:18][CH:19]([CH2:23][CH:15]2[CH2:16]4)[CH2:20]3)[C:5]2=[C:6]3[CH:12]=[CH:11][NH:10][C:7]3=[N:8][CH:9]=[C:4]2[NH:3]1.Cl.[NH2:28][CH2:29][C:30]#[N:31].ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.O.C(OCC)(=O)C>[C:29]([CH2:30][NH:31][C:24]([C:17]12[CH2:22][CH:21]3[CH2:20][CH:19]([CH2:23][CH:15]([CH:14]3[N:13]3[C:5]4=[C:6]5[CH:12]=[CH:11][NH:10][C:7]5=[N:8][CH:9]=[C:4]4[NH:3][C:2]3=[O:1])[CH2:16]1)[CH2:18]2)=[O:25])#[N:28]

Participants

9

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11491918Aminoacetonitrile hydrochlorideHCID 66924253HCID 66924253, compound

Product 1

HCID 57928295HCID 57928295, compoundYield 41.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(2-Oxo-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-1(2H)-yl)adamantan-1-carboxylic acid (50 mg) was suspended in N,N-dimethyl formamide (1 ml). To the suspension were added aminoacetonitrile hydrochloride (17 mg), 1-hydroxybenzotriazole (28 mg), diisopropylethylamine (62 μl), and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (41 mg) successively, and the mixture was stirred overnight at ambient temperature. To the reaction solution were added ethyl acetate and water, and the organic layer was extracted. The organic layer was washed with saturated brine, dried over magnesium sulfate, and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol) to obtain N-(cyanomethyl)-4-(2-oxo-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-1(2H)-yl)adamantan-1-carboxamide (23 mg).

Workup

  1. extractionthe organic layer was extracted
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform:methanol)

Sources & evidence

ORD record
ord-692b2340da194fdfa7970234bb84e1bb
Source dataset
uspto-grants-2011_02
Patent number
US07879844B2

Reaction notes

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