3-Pyridinecarboxaldehyde → HCID 22730881, compound

HRID 1785833Notes

Reaction equation

HRID 1785833 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:20]([NH:23][C:24](=[O:37])[C:25]2[CH:30]=[CH:29][C:28]([C:31]3[CH2:32][CH2:33][NH:34][CH2:35][CH:36]=3)=[CH:27][CH:26]=2)(=[O:22])=[O:21])[CH:7]=[CH:8][C:9]=1[NH:10][CH2:11][CH2:12][S:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O-:3])=[O:2].[BH3-]C#N.[Na+].[OH-].[Na+].[N:44]1[CH:49]=[CH:48][CH:47]=[C:46]([CH:50]=O)[CH:45]=1>C(O)(=O)C.CO>[N+:1]([C:4]1[CH:5]=[C:6]([S:20]([NH:23][C:24](=[O:37])[C:25]2[CH:30]=[CH:29][C:28]([C:31]3[CH2:36][CH2:35][N:34]([CH2:50][C:46]4[CH:45]=[N:44][CH:49]=[CH:48][CH:47]=4)[CH2:33][CH:32]=3)=[CH:27][CH:26]=2)(=[O:21])=[O:22])[CH:7]=[CH:8][C:9]=1[NH:10][CH2:11][CH2:12][S:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 103713-PyridinecarboxaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 22730872HCID 22730872, compound

Product 1

HCID 22730881HCID 22730881, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of Example 340A (65 mg, 0.1 mmol), NaBH3CN (48 mg, 0.75 mmol), 2N NaOH (0.15 mL), and 3-pyridinecarboxaldehyde (214 mg, 2 mmol) in acetic acid (0.5 mL) and methanol (1 mL) was stirred for 16 hours. The reaction mixture was concentrated, dissolved in 1:1 DMSO/methanol (1.0 mL) and purified by reverse phase preparative HPLC using 20-90% acetonitrile/water containing 0.1% TFA to provide the desired product. MS (ESI(−)) m/e 628 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 8.78 (br t, 1H), 8.70 (d, 1H), 8.70 (dd, 1H), 8.60 (d, 1H), 8.05 (m, 1H), 7.95 (d, 2H), 7.62 (d, 2H), 7.60 (dd, 1H), 7.40-7.15 (m, 6H), 6.35 (m, 1H), 4.52 (d, 2H), 3.92 (m, 4H),3.45 (t, 4H), 2.82 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in 1:1 DMSO/methanol (1.0 mL)
  3. custompurified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-12b7908ed45c4f35a99a109b781a7540
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

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