Chloroacetaldehyde → HCID 11386975, compound

HRID 2105517Notes

Reaction equation

HRID 2105517 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH:10]3[CH2:15][CH2:14][N:13]([CH2:16][C:17]4[CH:22]=[CH:21][C:20]([C:23]5[N:28]=[CH:27][C:26]([C:29](=[NH:31])[NH2:30])=[CH:25][C:24]=5[C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)=[CH:19][CH:18]=4)[CH2:12][CH2:11]3)[NH:7][C:6]=2[CH:38]=1.Cl[CH2:40][CH:41]=O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH:10]3[CH2:15][CH2:14][N:13]([CH2:16][C:17]4[CH:22]=[CH:21][C:20]([C:23]5[C:24]([C:32]6[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=6)=[CH:25][C:26]([C:29]6[NH:30][CH:40]=[CH:41][N:31]=6)=[CH:27][N:28]=5)=[CH:19][CH:18]=4)[CH2:12][CH2:11]3)[NH:7][C:6]=2[CH:38]=1

Participants

5

Reactant 3

HCID 33ChloroacetaldehydeHCID 10340Sodium CarbonateHCID 57808550HCID 57808550, compound

Product 1

HCID 11386975HCID 11386975, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 6-(4-{[4-(6-fluoro-1H-benzimidazol-2-yl)piperidin-1-yl]methyl)phenyl)-5-phenylpyridine-3-carboximidamide (3-2, 0.030 g, 0.059 mmol) in Dioxane (1.5 mL) was added chloroacetaldehyde (50% solution in H2O, 0.019 mL, 0.119 mmol) followed by sodium carbonate (0.016 mg, 0.149 mmol). The reaction was heated to 110° C. for 1 hr. The mixture was cooled and partitioned between saturated aqueous sodium bicarbonate and CH2Cl2 and extracted 3×. The combined organics were dried (anhd. Na2SO4), filtered and concentrated. The residue was purified by silica gel chromatography (6-8% MeOH in CH2Cl2). 1H-NMR (500 MHz, d6 DMSO) δ 12.83 (s, 1H), 12.31 (s, 1H), 9.21 (d, J=1.95, 1H), 8.74 (s, 1H), 8.30 (d, J=2.2, 1H), 7.08-7.42 (m, 12H), 6.97 (bs, 1H), 3.61 (bs, 2H), 3.50 (bs, 1H), 3.13 (bs, 2H), 2.87 (bs, 2H), 1.98 (bs, 2H), 1.84 (bs 2H). HRMS m/z (M+H) Calcd: 529.2511, found: 529.2532.

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned between saturated aqueous sodium bicarbonate and CH2Cl2
  3. extractionextracted 3×
  4. dry with materialThe combined organics were dried (anhd. Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (6-8% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-5a2b8b0686d44b0396a2f42de0d309e1
Source dataset
uspto-grants-2009_08
Patent number
US07579355B2

Reaction notes

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