1,1'-Carbonyldiimidazole → HCID 123632245, compound

HRID 1509229Notes

Reaction equation

HRID 1509229 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:22][C:21]([NH2:30])=[C:20]([CH2:31][NH2:32])[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C1N=CN([C:39](N2C=NC=C2)=[O:40])C=1>C1COCC1>[C:1]([O:5][C:6](=[O:33])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:23]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)=[CH:22][C:21]4[NH:30][C:39](=[O:40])[NH:32][CH2:31][C:20]=4[N:19]=3)=[CH:16][CH:17]=2)[CH2:9][CH2:10][CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 123244203HCID 123244203, compound

Product 1

HCID 123632245HCID 123632245, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl(1-(4-(5-amino-6-(aminomethyl)-3-phenylpyridin-2-yl)phenyl)cyclobutyl)carbamate (113 mg, 0.25 mmol) in dry THF (2 ml) was added CDI (41 mg, 0.25 mmol) under nitrogen. The resulting mixture was stirred for 1 h at 60 C and concentrated to dryness under reduced pressure. The resulting residue was purified by Biotage silica gel chromatography (gradient 0 to 5% MeOH in DCM) to give the title compound (71 mg, 59%). 1H NMR (500 MHz, CDCl3): 8.91 (1H, br s), 7.19-7.11 (7H, m), 7.00-6.97 (3H, m), 5.73 (1H, s), 4.93 (1H, s), 4.65 (2H, s), 2.52-2.20 (4H, m), 2.00-1.95 (1H, m), 1.79-1.65 (1H, m), 1.40-1.10 (9H, br)

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  2. customThe resulting residue was purified by Biotage silica gel chromatography (gradient 0 to 5% MeOH in DCM)

Sources & evidence

ORD record
ord-513a50c8df8b44bdbf3253336222cf13
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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