Sodium Methoxide → HCID 10230712, compound

HRID 433896Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([C:8]2[N:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[N:5]=[C:4]([NH:14][S:15]([CH2:18][CH2:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)(=[O:17])=[O:16])[C:3]=1[O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[O:37][CH3:38].[CH3:39][O-:40].[Na+]>CO>[CH3:39][O:40][C:2]1[N:7]=[C:6]([C:8]2[N:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[N:5]=[C:4]([NH:14][S:15]([CH2:18][CH2:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)(=[O:17])=[O:16])[C:3]=1[O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[O:37][CH3:38]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of N-[6-chloro-5-(2-methoxyphenoxy)-2-(3-pyridazinyl )-4-pyrimidinyl]-2-(1-naphthyl)ethanesulfonamide (0.088 g, 0.17 mmol) (Preparation 14) in methanol (5 ml) was added sodium methoxide (25% w/v in methanol, 1.0 ml). The mixture was stirred vigorously for 72 hours at 60° C. and then quenched with aqueous hydrochloric acid (2 M, 1 ml). Ice-cold water (2 ml) was added and a white precipitate formed. The resultant mixture was partitioned between water (5 ml) and dichloromethane (3×10 ml). The combined organic extracts were washed with water (3×10 ml), dried (magnesium sulfate) and concentrated under vacuum to give the title compound as a yellow solid (95% pure by HPLC). (0.065 g).

Workup

customquenched with aqueous hydrochloric acid (2 M, 1 ml)
additionIce-cold water (2 ml) was added
customa white precipitate formed
customThe resultant mixture was partitioned between water (5 ml) and dichloromethane (3×10 ml)
washThe combined organic extracts were washed with water (3×10 ml)
dry with materialdried (magnesium sulfate)
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-a6fce0b77ea5444f85c437cfcba0767b
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06670362B2

Reaction notes

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