HCID 68509346, compound → 9h-Fluoren-9-ylmethyl 4-[4-(aminocarbonyl)-1h-benzimidazol-2-yl]piperidin-4-ylcarbamate

HRID 12634Notes

Reaction equation

HRID 12634 reaction equation
[NH2:1][C:2]([C:4]1[C:12]2[N:11]=[C:10]([C:13]3([NH:29][C:30]([O:32][CH2:33][CH:34]4[C:46]5[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=5[C:40]5[C:35]4=[CH:36][CH:37]=[CH:38][CH:39]=5)=[O:31])[CH2:18][CH2:17][N:16](C(OCC4C=CC=CC=4)=O)[CH2:15][CH2:14]3)[NH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)=[O:3]>CO.C(O)(=O)C.[Pd]>[NH2:1][C:2]([C:4]1[C:12]2[N:11]=[C:10]([C:13]3([NH:29][C:30](=[O:31])[O:32][CH2:33][CH:34]4[C:35]5[CH:36]=[CH:37][CH:38]=[CH:39][C:40]=5[C:41]5[C:46]4=[CH:45][CH:44]=[CH:43][CH:42]=5)[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[NH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)=[O:3]

Participants

5

Reactant 1

HCID 68509346HCID 68509346, compound

Product 1

HCID 469115899h-Fluoren-9-ylmethyl 4-[4-(aminocarbonyl)-1h-benzimidazol-2-yl]piperidin-4-ylcarbamateYield 69%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of Example 49A (0.175 g, 0.3 mmol) and 10% Pd/C (0.015 g) in MeOH (5 ml) and acetic acid (0.2 ml), was stirred overnight under a H2 atmosphere at room temperature. The mixture was filtered through a pad of silica then concentrated under vacuum. The residue was purified by HPLC on a C18 column with 0-100% CH3CN/H2O/0.1% TFA to provide 0.095 g (69%) of the desired product. MS (ESI) m/e 482 (M+H)+. 1H NMR (DMSO-D6) δ ppm 8.55 (s, 1H), 8.42 (s, 1H), 8.15 (s, 1H), 7.82-7.91 (m, 3H), 7.65-7.78 (s, 3H) 7.42 (d, J=7.67 Hz 2H), 7.29-7.34 (m, 2H), 4.31 (d, J=7.06 Hz, 2H), 3.5-3.28 (m, 7H), 2.42 (s, 2H).

Workup

  1. filtrationThe mixture was filtered through a pad of silica
  2. concentrationthen concentrated under vacuum
  3. customThe residue was purified by HPLC on a C18 column with 0-100% CH3CN/H2O/0.1% TFA

Sources & evidence

ORD record
ord-a092888c86624ae681dbaa94eb001e74
Source dataset
uspto-grants-2010_06
Patent number
US07728026B2

Reaction notes

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