N-methyl-2-pyrrolidone → HCID 71656473, compound

HRID 877591Notes

Reaction equation

Cl[C:2]1[CH:9]=[C:8]([NH:10][C@@H:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C@H:12]([OH:15])[CH2:13][OH:14])[C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[S:22]1[C:26]2[CH:27]=[C:28]([NH2:31])[CH:29]=[CH:30][C:25]=2[N:24]=[CH:23]1.CN1C(=O)CCC1>O>[S:22]1[C:26]2[CH:27]=[C:28]([NH:31][C:2]3[CH:9]=[C:8]([NH:10][C@@H:11]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C@H:12]([OH:15])[CH2:13][OH:14])[C:5]([C:6]#[N:7])=[CH:4][N:3]=3)[CH:29]=[CH:30][C:25]=2[N:24]=[CH:23]1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 6-chloro-4-((1S,2S)-2,3-dihydroxy-1-phenylpropylamino)nicotinonitrile (0.108 g, 0.356 mmol), benzo[d]thiazol-6-amine (0.187 g, 1.244 mmol) and NMP (1.422 mL) was stirred at 150° C. for 1 hour in a microwave reactor. The vessel was cooled to room temperature, diluted with water and filtered. Following drying on a buchner funnel, 6-(benzo[d]thiazol-6-ylamino)-4-((1S,2S)-2,3-dihydroxy-1-phenylpropylamino)nicotinonitrile (0.122 g, 0.292 mmol, 82% yield) was collected as a yellowish solid. LC-MS (m/z, M+1=418), Waters sunfire 4.6×50 mm C18 Sum 4 min/1 min hold time 0-100% (A-B) A=10% MeOH-90% water-0.1% TFA, B=90% MeOH-10% water-0.1% TFA RT=2.06.

Workup

temperatureThe vessel was cooled to room temperature
filtrationfiltered
customFollowing drying on a buchner funnel

Sources & evidence

ORD record: ord-26049b5c8e834893a83915e7a7d16778
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987311B2

Reaction notes

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