Acetic Acid → HCID 118235471, compound

HRID 627000Notes

Reaction equation

HRID 627000 reaction equation
[F:1][CH:2]([F:38])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]([C:12]1[N:16]2[CH:17]=[C:18]([C:21]3[CH:22]=[N:23][C:24]([N:27]4[CH2:32][CH2:31][CH:30]([C:33]([O:35]C)=[O:34])[CH2:29][CH2:28]4)=[N:25][CH:26]=3)[CH:19]=[CH:20][C:15]2=[N:14][C:13]=1[CH3:37])[CH3:11].O.[OH-].[Li+].C(O)(=O)C>C1COCC1.O>[F:38][CH:2]([F:1])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]([C:12]1[N:16]2[CH:17]=[C:18]([C:21]3[CH:26]=[N:25][C:24]([N:27]4[CH2:32][CH2:31][CH:30]([C:33]([OH:35])=[O:34])[CH2:29][CH2:28]4)=[N:23][CH:22]=3)[CH:19]=[CH:20][C:15]2=[N:14][C:13]=1[CH3:37])[CH3:11]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 168937Lithium hydroxide, monohydrateHCID 118235582HCID 118235582, compound

Product 1

HCID 118235471HCID 118235471, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 308 (0.28 g, 0.54 mmol) in THF (4 mL) at room temperature was added lithium hydroxide monohydrate (0.04 g, 0.81 mmol) in water (1 mL). The mixture was stirred for 2 h. The solution was adjusted to pH 6 by dropwise addition of acetic acid. The volatiles were removed in vacuo and the residue was treated with acetone (2 mL), causing a thick solid precipitate to form. The mixture was filtered and washed on the sinter with water and acetone, then dried in vacuo, to give the title compound (0.216 g, 79%) as a white solid. δH (400 MHz, DMSO-d6) 8.59 (s, 2H), 8.59 (s), 8.33 (s, 1H), 8.33 (s), 7.56 (dd, 1H, J 7.5, 1.3 Hz), 7.45 (m, 2H), 7.33 (m, 1H), 7.27 (m, 1H), 7.16 (d, 1H, J 8.1 Hz), 7.13 (t, 1H, J 78 Hz), 4.96 (m, 1H), 4.47 (m, 2H), 3.10 (m, 2H), 2.18 (m, 1H), 1.80 (m, 2H), 1.72 (m, 9H), 1.49 (m, 2H). LCMS (pH 3): MH+ 508.8, RT 1.77 minutes.

Workup

  1. customThe volatiles were removed in vacuo
  2. additionthe residue was treated with acetone (2 mL)
  3. customto form
  4. filtrationThe mixture was filtered
  5. washwashed on the sinter with water and acetone
  6. customdried in vacuo

Sources & evidence

ORD record
ord-e13e67af5cf44d10b6153670eb9b0250
Source dataset
uspto-grants-2016_04
Patent number
US09309243B2

Reaction notes

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