Sodium Nitrite → HCID 178432129, compound

HRID 1869281Notes

Reaction equation

HRID 1869281 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.[N:38]([O-])=O.[Na+]>CC(O)=O>[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[N:26]=[N:38][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

4

Reactant 2

HCID 23668193Sodium NitriteHCID 579860706-(4-{[4-(2-methyl-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-5-phenylpyridine-2,3-diamine

Product 1

HCID 178432129HCID 178432129, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

6-(4-{[4-(2-methyl-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-5-phenylpyridine-2,3-diamine (4-4, 0.052 g, 0.106 mmol) was dissolved in 1 ml HOAc. NaNO2 (0.008 g, 0.117 mmol) was added. After 1 h the reaction was concentrated in vacuo and diluted with saturated aqueous NaHCO3. The mixture was extracted 3× with DCM. The combined extracts were dried over Na2SO4, filtered and concentrated to afford pure 5-(4-{[4-(2-methyl-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-6-phenyl-1H-[1,2,3]triazolo[4,5-b]pyridine (5-1). 1H NMR (CDCl3) δ 8.42 (s, 1H), 7.73 (m, 1H), 7.59 (m, 1H), 7.38 (d, 2H, J=8.0 Hz), 7.31 (m, 4H), 7.22 (m, 4H), 4.19 (m, 1H), 3.64 (s, 2H), 3.10 (d, 2H, J=12.0 Hz), 2.67 (s, 3H), 2.59 (m, 2H), 2.20 (t, 2H, J=11.6 Hz), 1.86 (d, 2H, J=10.0 Hz). MS m/z (M+H)=500.22.

Workup

  1. concentrationAfter 1 h the reaction was concentrated in vacuo
  2. additiondiluted with saturated aqueous NaHCO3
  3. extractionThe mixture was extracted 3× with DCM
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bb02871e5ca54006803717208ff67c37
Source dataset
uspto-grants-2009_12
Patent number
US07638530B2

Reaction notes

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