Lithium Hydroxide → HCID 75202188, compound

HRID 1506798Notes

Reaction equation

HRID 1506798 reaction equation
[OH-].[Li+].[O:3]=[C:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:19]=[N:18][C:17]([NH:20][C:21]4[CH:22]=[N:23][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:26]=4)=[CH:16][N:15]=3)=[CH:11][CH:12]=2)[CH2:7][CH2:6][C:5]1([CH2:36][C:37]([O:39]CC)=[O:38])[CH2:31][C:32]([F:35])([F:34])[F:33]>C(O)C.O>[O:3]=[C:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:19]=[N:18][C:17]([NH:20][C:21]4[CH:22]=[N:23][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:25][CH:26]=4)=[CH:16][N:15]=3)=[CH:11][CH:12]=2)[CH2:7][CH2:6][C:5]1([CH2:36][C:37]([OH:39])=[O:38])[CH2:31][C:32]([F:34])([F:35])[F:33]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 90135532HCID 90135532, compound

Product 1

HCID 75202188HCID 75202188, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

Lithium hydroxide (0.114 g, 2.72 mmol) was added to a solution of 14B2 (0.3 g, 0.543 mmol) in 6 mL of ethanol-water (3:1) mixture, and the mixture was stirred at room temperature for 5 h. After the solvent was removed in vacuo, the residue was diluted with water. The aqueous layer was acidified with addition of saturated citric acid solution until pH 3 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 (0.2 g, 88%) as a solid. 1H NMR (300 MHz, DMSO-d6) δ 12.47 (s, 1H), 10.47 (s, 1H), 8.98 (dd, J1=1.9 Hz, J2=7.7 Hz, 2H), 8.53 (dd, J1=2.1 Hz, J2=8.7 Hz, 1H), 8.46 (s, 1H), 8.10-7.93 (m, 3H), 7.88 (d, J=8.7 Hz, 1H), 3.26-2.92 (m, 3H), 2.88-2.64 (m, 2H), 2.58-2.42 (m, 2H), 2.17 (m, 1H). ESI-MS m/z: 525 (M+H)+; HPLC purity: 97%.

Workup

  1. customAfter the solvent was removed in vacuo
  2. additionthe residue was diluted with water
  3. additionThe aqueous layer was acidified with addition of saturated citric acid solution until pH 3
  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-78cd6c3cdd464c7d948db08ccf09d98e
Source dataset
uspto-grants-2015_12
Patent number
US09221766B2

Reaction notes

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