Hydrochloric Acid → HCID 57808550, compound

HRID 2105516Notes

Reaction equation

HRID 2105516 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[C:30]([C:31]6[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=6)=[CH:29][C:26]([C:27]#[N:28])=[CH:25][N:24]=5)=[CH:19][CH:18]=4)[CH2:12][CH2:11]3)[NH:7][C:6]=2[CH:37]=1.[NH:38]1CCC(N2C3C=CC=CC=3NC2=O)CC1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.Cl.[OH-].[Na+]>C1COCC1>[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:24]=[CH:25][C:26]([C:27](=[NH:38])[NH2:28])=[CH:29][C:30]=5[C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=5)=[CH:19][CH:18]=4)[CH2:12][CH2:11]3)[NH:7][C:6]=2[CH:37]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 2733832Lithium HexamethyldisilazideHCID 11431759HCID 11431759, compound

Product 1

HCID 57808550HCID 57808550, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(4-{[4-(6-fluoro-1H-benzimidazol-2-yl)piperidin-1-yl]methyl}phenyl)-5-phenylnicotinonitrile (3-1, 0.050 g, 0.103 mmol, prepared according to Scheme 1, but substituting the appropriate amine for (1-4)) in anhydrous THF (3 mL)@0° C. was added LiHMDS (1 M in THF, 0.513 mL, 0.513 mmol). The reaction was allowed to warm to rt and stirred for 1.5 hr. 1M HCl (1.5 mL) was added and reaction stirred for 30 min. 1M NaOH (3 mL) was then added and the resulting mixture was extracted with CH2Cl2 (3×15 mL). The combined organics were dried (anhd. Na2SO4), filtered, and concentrated. Resulting material was triturated with ether and dried in vacuo. HRMS m/z (M+H) Calcd: 505.7571, found: 505.2544.

Workup

  1. customreaction
  2. stirringstirred for 30 min
  3. extractionthe resulting mixture was extracted with CH2Cl2 (3×15 mL)
  4. dry with materialThe combined organics were dried (anhd. Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customResulting material was triturated with ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-108fb4d076b9449b876a9ce0483af6c7
Source dataset
uspto-grants-2009_08
Patent number
US07579355B2

Reaction notes

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