Sodium Hydroxide → HCID 86614808, compound

HRID 1992794Notes

Reaction equation

HRID 1992794 reaction equation
N1C(N[C:7]([C:9]2[CH:43]=[CH:42][C:12]([CH2:13][N:14]3[C:18]([C:19]([NH:21][C:22]4[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=4)=[O:20])=[CH:17][C:16]([C:33]4[CH:38]=[C:37]([F:39])[C:36]([F:40])=[C:35]([F:41])[CH:34]=4)=[N:15]3)=[CH:11][CH:10]=2)=[O:8])=NN=N1.[OH-:44].[Na+]>C1COCC1.CO>[F:31][C:29]([F:32])([F:30])[O:28][C:25]1[CH:26]=[CH:27][C:22]([NH:21][C:19]([C:18]2[N:14]([CH2:13][C:12]3[CH:42]=[CH:43][C:9]([C:7]([OH:44])=[O:8])=[CH:10][CH:11]=3)[N:15]=[C:16]([C:33]3[CH:38]=[C:37]([F:39])[C:36]([F:40])=[C:35]([F:41])[CH:34]=3)[CH:17]=2)=[O:20])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178522672HCID 178522672, compound

Product 1

HCID 86614808HCID 86614808, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of the intermediate from step A (0.1 g, 0.18 mmol) in 10 ml of THF/MeOH was added 5 N NaOH (1 mL). After stirring the reaction at room temperature for 2 hours it was concentrated in vacuo. The residue was acidified with 1N HCl (10 ml) and was extracted with ethyl acetate, dried over anhydrous Na2SO4 filtered and concentrated in vacuo. This material was used in the next step without any further purification. 1H NMR (CD3OD, 500 MHz): 7.96 (d, J=8.2 Hz, 2H), 7.73 (d, J=8.9 Hz, 2H), 7.62 (t, J=7.1 Hz, 2H), 7.4 (s, 1H), 7.35 (d, J=8.2 Hz, 2H), 7.27 (d, J=8.7 Hz, 2H), 5.88 (s, 2H). LC-MS=4.0 min; (M+H)=536.0.

Workup

  1. customthe reaction at room temperature for 2 hours it
  2. concentrationwas concentrated in vacuo
  3. extractionwas extracted with ethyl acetate
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThis material was used in the next step without any further purification
  8. customLC-MS=4.0 min

Sources & evidence

ORD record
ord-6acfe4d339c8488faa02de5a6c814e23
Source dataset
uspto-grants-2010_01
Patent number
US07649009B2

Reaction notes

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