Ammonia → HCID 54552478, compound

HRID 52287Notes

Reaction equation

HRID 52287 reaction equation
[CH:1]1([N:6]([C@@H:11]2[CH2:16][C:15]3[C:17]([O:22]C)=[CH:18][CH:19]=[C:20]([F:21])[C:14]=3[O:13][CH2:12]2)[CH:7]2[CH2:10][CH2:9][CH2:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.N>Br>[CH:1]1([N:6]([C@@H:11]2[CH2:16][C:15]3[C:17]([OH:22])=[CH:18][CH:19]=[C:20]([F:21])[C:14]=3[O:13][CH2:12]2)[CH:7]2[CH2:10][CH2:9][CH2:8]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 22871221HCID 22871221, compound

Product 1

HCID 54552478HCID 54552478, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
120 °C

Procedure

(R)-3-(N-Cyclopentyl-N-cyclobutylamino)-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyran (0.53 g, 1.6 mmol) was dissolved in 47% HBr (15 mL) and stirred at 120° C. for 1.5 h. The solution was cooled by adding ice and alkalised by 14M ammonia. Extractive work-up gave 0.5 g of the title compound as a slightly brown oil. IR contained a typical OH-band at 3654 cm-1.

Workup

  1. temperatureThe solution was cooled
  2. additionby adding ice

Sources & evidence

ORD record
ord-fc90620444474edaa79b1c3ffdd89abd
Source dataset
uspto-grants-1997_04
Patent number
US05616610

Reaction notes

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