Water → 1,1-dioxo-3-(propan-2-ylamino)-4H-thieno[3,2-e][1,2,4]thiadiazine-6-carbonitrile

HRID 1975938Notes

Reaction equation

Br[C:2]1[S:10][C:9]2[S:8](=[O:12])(=[O:11])[N:7]=[C:6]([NH:13][CH:14]([CH3:16])[CH3:15])[NH:5][C:4]=2[CH:3]=1.[Cu][C:18]#[N:19].O.[OH-].[Na+]>CN(C)C=O>[C:18]([C:2]1[S:10][C:9]2[S:8](=[O:12])(=[O:11])[N:7]=[C:6]([NH:13][CH:14]([CH3:16])[CH3:15])[NH:5][C:4]=2[CH:3]=1)#[N:19]

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of 6-bromo-3-isopropylamino-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide (243 mg, 0.75 mmol) in dry N,N-dimethylformamide (2 ml) was added copper(I) cyanide (135 mg, 1.5 mmol) and the mixture was heated at 150° C. for 2 h under nitrogen. The dark mixture was allowed to cool to room temperature and water was added. The suspension was made basic by the addition of 1 N sodium hydroxide, filtered and the filtrate was acidified by the addition of 4 M hydrochloric acid. The resulting precipitate was purified by preparative hplc on a Source RPC 15 column using acetonitrile/water (20:80) with 0.1% TFA as eluent to afford 4 mg (2%) of the pure title compound; LC-MS: m/e 271 ((M+1)+).

Workup

temperatureto cool to room temperature
filtrationfiltered
additionthe filtrate was acidified by the addition of 4 M hydrochloric acid
customThe resulting precipitate was purified by preparative hplc on a Source RPC 15 column

Sources & evidence

ORD record: ord-b645fa9cc20247899fafa104d77ec6e0
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06225310B1

Reaction notes

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