Acetic Acid → 6-(4-{[4-(2-Methyl-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-3-nitro-5-phenylpyridin-2-amine

HRID 1869278Notes

Reaction equation

HRID 1869278 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=2)[C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:4][C:3]=1[N+:22]([O-:24])=[O:23].Cl.[CH3:26][C:27]1[N:31]([CH:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[C:30]2[CH:38]=[CH:39][CH:40]=[CH:41][C:29]=2[N:28]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(N(CC)CC)C.C(O)(=O)C>CN(C=O)C>[CH3:26][C:27]1[N:31]([CH:32]2[CH2:33][CH2:34][N:35]([CH2:12][C:11]3[CH:14]=[CH:15][C:8]([C:6]4[N:7]=[C:2]([NH2:1])[C:3]([N+:22]([O-:24])=[O:23])=[CH:4][C:5]=4[C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:9][CH:10]=3)[CH2:36][CH2:37]2)[C:30]2[CH:38]=[CH:39][CH:40]=[CH:41][C:29]=2[N:28]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 220613952-methyl-1-piperidin-4-yl-1H-benzimidazole hydrochlorideHCID 579860624-(6-Amino-5-nitro-3-phenylpyridin-2-yl)benzaldehyde

Product 1

HCID 579860756-(4-{[4-(2-Methyl-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-3-nitro-5-phenylpyridin-2-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(6-Amino-5-nitro-3-phenylpyridin-2-yl)benzaldehyde (4-2; 0.150 g, 0.470 mmol), 2-methyl-1-piperidin-4-yl-1H-benzimidazole hydrochloride (0.142 g, 0.564 mmol), and NaBH(OAc)3 (0.120 g, 0.564 mmol) were stirred in 2 ml of anhydrous DMF. Triethylamine (0.079 ml, 0.564 mmol) was added followed by addition of acetic acid (0.108 ml, 1.88 mmol). After 2 h the reaction was quenched with saturated aqueous NaHCO3 and extracted 3× with DCM. The combined extracts were dried over Na2SO4, filtered, and concentrated to afford pure 6-(4-{[4-(2-methyl-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-3-nitro-5-phenylpyridin-2-amine (4-3). 1H NMR (CDCl3) δ 8.48 (s, 1H), 7.68 (m, 1H), 7.57 (m, 1H), 7.36 (d, 2H, J=8.1 Hz), 7.27 (m overlapping with CHCl3), 7.20 (m, 2H), 7.16 (m, 2H), 4.15 (m, 1H), 3.58 (s, 2H), 3.05 (d, 2H, J=11.5 Hz), 2.63 (s, 3H), 2.55 (m, 2H), 2.17 (t, 2H, J=11.5 Hz), 1.83 (d, 2H, J=12.0 Hz). MS m/z (M+H)=519.18.

Workup

  1. customAfter 2 h the reaction was quenched with saturated aqueous NaHCO3
  2. extractionextracted 3× with DCM
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f79332a52b034d8dad086e4d330869d9
Source dataset
uspto-grants-2009_12
Patent number
US07638530B2

Reaction notes

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