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

HRID 1504895
Notes
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Reaction equation

HRID 1504895 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 469414773-Bromo-5-fluoropicolinonitrileHCID 59676894tert-Butyl ((3S,4S)-3-amino-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)carbamate

Product 1

HCID 90354174tert-butyl rel-{(3S,4S)-3-[(5-bromo-6-cyanopyridin-3-yl)amino]-1,1-dioxidotetrahydro-2H-thiopyran-4-yl}carbamate

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 13387N-methyl-2-pyrrolidoneSolvent

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

  1. filtrationThe reaction mixture was filtered
  2. washthe collected solids were washed with cold water
  3. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes