Diisopropylethylamine → tert-butyl rel-{(3S,4S)-3-[(5-bromo-6-cyanopyridin-3-yl)amino]-1,1-dioxidotetrahydro-2H-thiopyran-4-yl}carbamate

HRID 1504895Notes

Reaction equation

CCN(C(C)C)C(C)C.[Br:10][C:11]1[C:12]([C:18]#[N:19])=[N:13][CH:14]=[C:15](F)[CH:16]=1.[NH2:20][C@H:21]1[C@@H:26]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:25][CH2:24][S:23](=[O:36])(=[O:35])[CH2:22]1>CN1C(=O)CCC1.O>[Br:10][C:11]1[CH:16]=[C:15]([NH:20][C@H:21]2[C@@H:26]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:32])([CH3:33])[CH3:31])[CH2:25][CH2:24][S:23](=[O:36])(=[O:35])[CH2:22]2)[CH:14]=[N:13][C:12]=1[C:18]#[N:19]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of Hunig's base (2.69 ml, 15.4 mmol), 3-bromo-5-fluoropyridine-2-carbonitrile (1.55 g, 7.69 mmol), tert-butyl rel-[(3S,4S)-3-amino-1,1-dioxidotetrahydro-2H-thiopyran-4-yl]carbamate (2.51 g, 9.50 mmol) in NMP (8 ml) was heated to 150° C. for 30 minutes. The reaction mixture was diluted with water (50 mL) and stirred. The reaction mixture was filtered, and the collected solids were washed with cold water. The solids were dried under reduced pressure to afford tert-butyl rel-{(3S,4S)-3-[(5-bromo-6-cyanopyridin-3-yl)amino]-1,1-dioxidotetrahydro-2H-thiopyran-4-yl}carbamate. MS ESI calc'd. for C16H22BrN4O4S [M+H]+ 445 and 447. found 445 and 447.

Workup

filtrationThe reaction mixture was filtered
washthe collected solids were washed with cold water
customThe solids were dried under reduced pressure

Sources & evidence

ORD record: ord-127668054cb3498eb09432aeb506468d
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216173B2

Reaction notes

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