P-Anisidine → HCID 59656405, compound

HRID 2225070Notes

Reaction equation

HRID 2225070 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([NH:12][S:13]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]([NH2:26])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:8][CH2:7]1)=[O:5])[CH3:2].COC1C=CC(N)=CC=1.C(=O)(O)[O-].[Na+].[CH3:41][C:42]1[N:50]=[CH:49][CH:48]=[CH:47][C:43]=1[C:44](Cl)=[O:45]>C(Cl)Cl>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][CH:9]([NH:12][S:13]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]([NH:26][C:44]([C:43]3[C:42]([CH3:41])=[N:50][CH:49]=[CH:48][CH:47]=3)=[O:45])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 7732P-AnisidineHCID 516892Sodium BicarbonateHCID 129025982-Methylpyridine-3-carbonyl chlorideHCID 16105843HCID 16105843, compound

Product 1

HCID 59656405HCID 59656405, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-(4-Amino-naphthalene-1-sulfonylamino)-piperidine-1-carboxylic acid ethyl ester (0.26 g, 0.71 mmol) (prepared following the general procedure in Scheme 3, substituting 4-amino-piperidine-1-carboxylic acid ethyl ester for p-anisidine) in CH2Cl2 (10 mL) and aqueous saturated sodium bicarbonate solution (4 mL) was added 2-methyl nicotinic chloride (0.16 g, 1.07 mmol) and the resulting mixture was stirred at room temperature overnight. The organic layer was separated, dried over sodium sulfate and concentrated. Purification of the residue by column chromatography (2-5% MeOH/CH2Cl2) provided the B-24 (0.09g, 26%). 1H NMR (300 MHz, CDCl3) δ 8.61-8.66 (m, 2H), 8.34 (s, 1H), 8.19-8.28 (m, 1H), 7.94 (d, 2H), 7.60-7.70 (m, 2H), 7.28-7.31(m, 1H), 4.91(d, 1H), 4.03 (q, 2H), 3.85 (d, 2H), 3.20-3.32 (m, 1H), 2.80 (s, 2H), 2.63-2.74 (m, 2H), 1.67 (br s, 4H), 1.16-1.21 (m, 5H). LC/MS m/z 497 (M+H)+.

Workup

  1. customprepared
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customPurification of the residue by column chromatography (2-5% MeOH/CH2Cl2)
  6. customprovided the B-24 (0.09g, 26%)

Sources & evidence

ORD record
ord-ebdc5f04e77f499ca5c92a681d7d58a7
Source dataset
uspto-grants-2008_05
Patent number
US07378525B2

Reaction notes

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