Acetic Acid → HCID 10283821, compound

HRID 1840283Notes

Reaction equation

HRID 1840283 reaction equation
[CH3:1][C:2]1([CH3:31])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([CH:11]([N:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)[C:12]3[CH:24]=[CH:23][C:15]([C:16]([N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[O:17])=[CH:14][CH:13]=3)[C:4]=2[O:3]1.[N:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH:38]=O.CC(O)=O.C([BH3-])#N.[Na+]>CO>[CH3:31][C:2]1([CH3:1])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([CH:11]([N:25]3[CH2:26][CH2:27][N:28]([CH2:38][C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][N:32]=4)[CH2:29][CH2:30]3)[C:12]3[CH:24]=[CH:23][C:15]([C:16]([N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[O:17])=[CH:14][CH:13]=3)[C:4]=2[O:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 142732-PyridinecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 11742939HCID 11742939, compound

Product 1

HCID 10283821HCID 10283821, compoundYield 1,883%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

The title compound 9 was prepared by dissolving compound 5 (0.45 g, 0.98 mmol) in MeOH (10 mL) with 2-pyridine carboxaldehyde (110 μL, 1.18 mmol) and HOAc (3 μL, 50 μmol). Sodium cyanoborohydride (70 mg, 1.18 mmol) was added at 0° C. and reaction stirred 48 h at 25° C. Reaction was worked up by concentration in vacuo, extraction (CH2Cl2/K2CO3(aq)) and chromatography by reverse phase HPLC to give the title compound 9,461 mg(63%).

Workup

  1. customreaction
  2. customReaction
  3. concentrationwas worked up by concentration in vacuo, extraction (CH2Cl2/K2CO3(aq)) and chromatography by reverse phase HPLC

Sources & evidence

ORD record
ord-59530886033c466b9efbbe8fe949261b
Source dataset
uspto-grants-2004_01
Patent number
US06680318B2

Reaction notes

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