Lithium Hydroxide → HCID 117777841, compound

HRID 64153Notes

Reaction equation

HRID 64153 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([N:15]2[C:19]3[CH:20]=[CH:21][C:22]([C:24]4[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=4)=[CH:23][C:18]=3[N:17]=[CH:16]2)[CH:12]=[C:11]([NH:30][C:31](=[O:38])[CH2:32][C:33]([O:35]CC)=[O:34])[CH:10]=1.[OH-].[Li+]>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([N:15]2[C:19]3[CH:20]=[CH:21][C:22]([C:24]4[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=4)=[CH:23][C:18]=3[N:17]=[CH:16]2)[CH:12]=[C:11]([NH:30][C:31](=[O:38])[CH2:32][C:33]([OH:35])=[O:34])[CH:10]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 117777419HCID 117777419, compound

Product 1

HCID 117777841HCID 117777841, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound of Example 223 (20 mg, 0.0388 mmol) in THF (10 ml) was added aqueous solution of lithium hydroxide (4 mg, 0.0776 mmol, 2 eq) and the mixture was stirred at RT for 2 h. The mixture was quenched and extracted as in Example 1(d). The solvent was distilled off to afford the crude residue which was purified by preparative HPLC to give the pure product in 90% yield (25 mg). 1H NMR (400 MHz, DMSO-d6): δ 10.7 (s, 1H), 8.77 (s, 1H), 8.23 (s, 1H), 8.10 (s, 1H), 8.01 (s, 1H), 7.97 (s, 1H), 7.83 (s, 1H), 7.78 (d, 1H), 7.73 (d, 1H), 7.65 (d, 1H), 7.59 (s, 1H), 7.49 (t, 1H), 7.3 (t, 1H), 3.90 (s, 3H), 3.45 (s, 2H); LC-MS (ESI): Calculated mass: 487.15; Observed mass: 488.0 [M+H]+ (rt: 0.638 min).

Workup

  1. customThe mixture was quenched
  2. extractionextracted as in Example 1(d)
  3. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-681612aeb00d4d95b6d2ce91d2eeb06b
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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