Lithium Hydroxide → HCID 75202237, compound

HRID 1506802Notes

Reaction equation

HRID 1506802 reaction equation
[OH-].[Li+].[CH3:3][C:4]1[N:9]=[CH:8][C:7]([NH:10][C:11]2[N:16]=[N:15][C:14]([C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[C:23](=[O:27])[C:22]([CH2:33][C:34]([O:36]CC)=[O:35])([CH2:28][C:29]([F:32])([F:31])[F:30])[CH2:21][CH2:20]4)=[CH:13][CH:12]=2)=[CH:6][CH:5]=1>C(O)C.O>[CH3:3][C:4]1[N:9]=[CH:8][C:7]([NH:10][C:11]2[N:16]=[N:15][C:14]([C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[C:23](=[O:27])[C:22]([CH2:33][C:34]([OH:36])=[O:35])([CH2:28][C:29]([F:31])([F:32])[F:30])[CH2:21][CH2:20]4)=[CH:13][CH:12]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 90135606HCID 90135606, compound

Product 1

HCID 75202237HCID 75202237, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

Lithium hydroxide (0.042 g, 1 mmol) was added to a solution of 22B1 (0.125 g, 0.25 mmol) in 6 mL of ethanol-water (3:1) mixture, and the reaction mixture was stirred at room temperature for 8 h. After the solvent was removed in vacuo, the residue was dissolved in water. The aqueous layer was acidified by addition of saturated solution of citric acid until pH 4 was attained. The resulting solution was cooled to 0° C., and solids obtained were filtered off and dried under vacuum to afford the title compound (0.105 g, 89%) as a solid. 1H NMR (300 MHz, DMSO-d6): δ 12.4 (bs, 1H), 9.59 (s, 1H), 8.76 (d, J=2.7 Hz, 1H), 8.22 (dd, J1=2.7 Hz, J2=8.4 Hz, 1H), 8.11 (d, J=9.6 Hz, 1H), 8.05-7.97 (m, 3H), 7.25 (d, J=3.0 Hz, 1H), 7.23 (s, 1H), 3.15-2.95 (m, 3H), 2.84 (d, J=16.2 Hz, 1H), 2.78-2.65 (m, 1H), 2.58 (d, J=16.5 Hz, 1H), 2.46 (m, 1H), 2.43 (s, 3H), 2.19 (m, 1H). ESI-MS m/z: 471 (M+H)+; HPLC purity: 98%.

Workup

  1. customAfter the solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in water
  3. additionThe aqueous layer was acidified by addition of saturated solution of citric acid until pH 4
  4. temperatureThe resulting solution was cooled to 0° C.
  5. customsolids obtained
  6. filtrationwere filtered off
  7. customdried under vacuum

Sources & evidence

ORD record
ord-0a077d67c5764610b7c2f3277d854eba
Source dataset
uspto-grants-2015_12
Patent number
US09221766B2

Reaction notes

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