1,1'-Carbonyldiimidazole → 5-(4-{[4-(2-methyl-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-6-phenyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 1869280Notes

Reaction equation

HRID 1869280 reaction equation
[CH3:1][C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[N:25]=[C:24]([NH2:26])[C:23]([NH2:27])=[CH:22][C:21]=4[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:16][CH:15]=3)[CH2:9][CH2:8]2)[C:5]2[CH:34]=[CH:35][CH:36]=[CH:37][C:4]=2[N:3]=1.[C:38](N1C=CN=C1)(N1C=CN=C1)=[O:39]>C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>[CH3:1][C:2]1[N:6]([CH:7]2[CH2:8][CH2:9][N:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[N:25]=[C:24]5[NH:26][C:38](=[O:39])[NH:27][C:23]5=[CH:22][C:21]=4[C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)=[CH:16][CH:15]=3)[CH2:11][CH2:12]2)[C:5]2[CH:34]=[CH:35][CH:36]=[CH:37][C:4]=2[N:3]=1

Participants

5

Reactant 2

HCID 682631,1'-Carbonyldiimidazole2×HCID 579860706-(4-{[4-(2-methyl-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-5-phenylpyridine-2,3-diamine

Product 1

HCID 112837005-(4-{[4-(2-methyl-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-6-phenyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

6-(4-{[4-(2-Methyl-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-5-phenylpyridine-2,3-diamine (4-4, 0.046 g, 0.094 mmol) was dissolved in 1 ml DCM and 1,1′-carbonyldiimidazole (0.017 g, 0.104 mmol) was added. After 8 h additional 1,1′-carbonyldiimidazole (0.017 g, 0.104 mmol) was added. After stirring overnight the reaction was diluted with saturated aqueous Na2CO3. The mixture was extracted 3× with DCM then 1× with iso-BuOH. Purification by flash column chromatography (95:5 to 90:10 DCM/MeOH) afforded 5-(4-{[4-(2-methyl-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-6-phenyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (4-5). 1H NMR (CDCl3) δ 7.69 (m, 1H), 7.55 (m, 1H), 7.27-7.16 (m, 9H), 7.08 (m, 2H), 6.76 (s, 1H), 4.12 (m, 1H), 3.34 (s, 2H), 2.96 (d, 2H), 2.61 (s, 3H), 2.52 (m, 2H), 2.27 (m, 2H), 1.79 (d, 2H, J=10.0 Hz). MS m/z (M+H)=515.16.

Workup

  1. extractionThe mixture was extracted 3× with DCM
  2. customPurification by flash column chromatography (95:5 to 90:10 DCM/MeOH)

Sources & evidence

ORD record
ord-2b849493e2fb452eb0590e42d95ea958
Source dataset
uspto-grants-2009_12
Patent number
US07638530B2

Reaction notes

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