Ammonium Hydroxide → HCID 57942163, compound

HRID 1898019Notes

Reaction equation

HRID 1898019 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:16]([C:22]([C:24]3[CH:25]=[N:26][C:27](Cl)=[CH:28][CH:29]=3)=[O:23])=[N:17][CH:18]=[C:19]([Cl:21])[CH:20]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[NH4+:32]>C1COCC1>[NH2:32][C:27]1[N:26]=[CH:25][C:24]([C:22]([C:16]2[C:15]([NH:14][S:11]([C:8]3[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:10][CH:9]=3)(=[O:12])=[O:13])=[CH:20][C:19]([Cl:21])=[CH:18][N:17]=2)=[O:23])=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 57942262HCID 57942262, compound

Product 1

HCID 57942163HCID 57942163, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A sealed tube was charged with 4-tert-butyl-N-[5-chloro-2-(6-chloro-pyridine-3-carbonyl)-pyridin-3-yl]-benzenesulfonamide (320 mg, 0.631 mmol), concentrated ammonium hydroxide (3.2 mL), and THF (3.2 mL). The tube was sealed and stirred for 3 days at 100° C. The solvents were subsequently removed in vacuo and the residue purified by automated flash chromatography to provide the desired aminopyridine: 1H NMR (400 MHz, CDCl3) δ 10.72 (bs, 1H), 8.69 (d, 1H), 8.28 (dd, 1H), 8.16 (dd, 1H), 8.02 (dd, 1H), 7.71 (d, 2H), 7.40 (d, 2H), 6.46 (d, 1H), 5.00 (bs, 2H), 1.24 (s, 9H); MS (ES) M+H expect 445.1. found 445.1.

Workup

  1. customThe tube was sealed
  2. customThe solvents were subsequently removed in vacuo
  3. customthe residue purified by automated flash chromatography

Sources & evidence

ORD record
ord-aa65437af1594d65b3b661fc5b323737
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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