Hydrazine hydrate (1:1) → HCID 86727586, compound

HRID 519232Notes

Reaction equation

HRID 519232 reaction equation
C([O:3][C:4](=O)[C@H:5]([N:7]1[C:12]2[CH:13]=[CH:14][C:15]([Br:17])=[CH:16][C:11]=2[O:10][CH2:9][C:8]1=S)[CH3:6])C.O.[NH2:21][NH2:22]>CCO>[Br:17][C:15]1[CH:16]=[C:11]2[C:12]([N:7]3[C:8]([CH2:9][O:10]2)=[N:22][NH:21][C:4](=[O:3])[C@H:5]3[CH3:6])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86727632HCID 86727632, compound

Product 1

HCID 86727586HCID 86727586, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of (R)-2-(7-bromo-3-thioxo-2,3-dihydro-benzo[1,4]oxazin-4-yl)-propionic acid ethyl ester (60 g, 174 mmol) in EtOH (800 mL) was added hydrazine hydrate (98%, 17.4 g, 349 mmol) and the reaction mixture was stirred at ambient temperature overnight. The precipitate was collected by filtration and washed with cold EtOH (3×80 mL) to give (R)-7-bromo-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (32.5 g, 59%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 10.82 (s, 1H), 7.23 (s, 1H), 7.21 (s, 2H), 4.78 (q, J=6.8 Hz, 1H), 4.68-4.60 (m, 2H), 1.29 (d, J=6.8 Hz, 3H). SFC (Table 1, Method 31) Rt=6.114 min.; [α]D20=−342.08 (C=0.002 g/mL in methanol).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with cold EtOH (3×80 mL)

Sources & evidence

ORD record
ord-7dc7a7ac82a649b58dbe447341fb33e0
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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