Ammonia → HCID 20227229, compound

HRID 1731817Notes

Reaction equation

HRID 1731817 reaction equation
[F:1][C:2]1[C:3]([C:22]2[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=2)=[C:4]2[O:9][CH2:8][CH:7]([CH3:10])[N:6]3[CH:11]=[C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:13](=[O:16])[C:14]([CH:15]=1)=[C:5]23.[NH3:32]>O1CCCC1>[F:1][C:2]1[C:3]([C:22]2[CH:27]=[CH:26][C:25]([S:28]([NH2:32])(=[O:30])=[O:29])=[CH:24][CH:23]=2)=[C:4]2[O:9][CH2:8][CH:7]([CH3:10])[N:6]3[CH:11]=[C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:13](=[O:16])[C:14]([CH:15]=1)=[C:5]23

Participants

4

Reactant 2

HCID 222AmmoniaHCID 20227234HCID 20227234, compound

Product 1

HCID 20227229HCID 20227229, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Ethyl 9-fluoro-10-(4-chlorosulfonylphenyl)-3-methyl-7-oxo-2,3-dihydro-(7H)-pyrido-(1,2,3-de)-1,4-benzoxazine-6-carboxylate (0.5 g) was dissolved in dry tetrahydrofuran (80 ml) and the resulting solution was cooled to -78° C. with stirring. Ammonia (5 ml) was condensed into the reaction mixture and the yellow suspension was warmed gradually to ambient temperature over 16 hours. Solvent was removed in vacuo and the residue was triturated with water and filtered. Drying in vacuo afforded a solid (0.3 g, 56% yield): m.p. >250° C. NMR (DMSO-d6, 250 MHz): 8.74 (s, 1H), 7.96 (d, 2H, J=10 Hz), 7.74 (d, 2 H, J= PG,91 10 Hz), 7.60 (d, 1H, J=10 Hz), 7.50 (s, 2H), 4.90-4.75 (m, 1H), 4.55-4.45 (m, 2H), 4.25 (q, 2H, J=7 Hz), 1.45 (d, 3H, J=7 Hz), 1.30 (t, 3H, J=7 Hz).

Workup

  1. customcondensed into the reaction mixture
  2. temperaturethe yellow suspension was warmed gradually to ambient temperature over 16 hours
  3. customSolvent was removed in vacuo
  4. customthe residue was triturated with water
  5. filtrationfiltered
  6. customDrying in vacuo

Sources & evidence

ORD record
ord-1835fb4dd8db4ed3b5e9acb581292ce4
Source dataset
uspto-grants-1986_11
Patent number
US04623650

Reaction notes

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