Sodium Hydroxide → HCID 86641107, compound

HRID 1809619Notes

Reaction equation

HRID 1809619 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[N:14]=[C:13]([NH:15][C:16]3[C:21]([S:22][C:23]4[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[CH:25][CH:24]=4)=[CH:20][C:19]([O:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[CH:18][N:17]=3)[S:12][N:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[OH-].[Na+:41]>CCO>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[N:14]=[C:13]([N-:15][C:16]3[C:21]([S:22][C:23]4[CH:32]=[CH:31][C:26]([C:27]([O-:29])=[O:28])=[CH:25][CH:24]=4)=[CH:20][C:19]([O:33][C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)=[CH:18][N:17]=3)[S:12][N:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Na+:41].[Na+:41]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67487272HCID 67487272, compound

Product 1

HCID 86641107HCID 86641107, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 4-(2-(3-(1-acetylpiperidin-4-yl)-1,2,4-thiadiazol-5-ylamino)-5-phenoxypyridin-3-ylthio)benzoate (0.15 g, 0.26 mmol) in EtOH was treated with NaOH (0.56 mL, 0.56 mmol). The solution was stirred at 60° C. for 1 hour. The solution was concentrated to give sodium (3-(1-acetylpiperidin-4-yl)-1,2,4-thiadiazol-5-yl)(3-(4-carboxylatophenylthio)-5-phenoxypyridin-2-yl)amide as a solid. To this salt was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.066 g, 0.35 mmol), 1-hydroxybenzotriazole hydrate (0.053 g, 0.35 mmol) in DMF (2 mL). N1,N1-dimethylethane-1,2-diamine (0.038 mL, 0.35 mmol) and DIEA (0.060 mL, 0.35 mmol) were added. The reaction stirred at 50° C. for 3 hours. The solution was then diluted with water, extracted with dichloromethane and concentrated. The crude material was purified via reverse phase HPLC to afford 4-(2-(3-(1-acetylpiperidin-4-yl)-1,2,4-thiadiazol-5-ylamino)-5-phenoxypyridin-3-ylthio)-N-(2-(dimethylamino)ethyl)benzamide (0.064 g, 36% yield). 1H NMR (CDCl3) δ 1.76-1.88 (m, 2H), 2.04-2.12 (m 2H), 2.10 (s, 3H), 2.25 (s, 6H), 2.50 (t, 2H), 2.82 (t, 1H), 3.00-3.06 (m, 1H), 3.20 (t, 1H), 3.48 (dd, 2H), 3.87 (d, 1H), 4.54 (d, 1H), 6.80 (bs, 1H), 7.02 (d, 1H), 7.14-7.19 (m, 3H), 7.38 (t, 2H), 7.67 (d, 1H), 7.71 (d, 2H), 8.30 (d, 1H), 9.20 (bs, 1H).

Workup

  1. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-df6d282455d54cc78363338865525a59
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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