Hydrochloric Acid → HCID 19085003, compound

HRID 962944Notes

Reaction equation

HRID 962944 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:7]([CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][C:16]([C:20]([O:22]CC)=[O:21])=[CH:17][CH:18]=2)[CH:13]=[N:12]1)=[O:8].O1CCCC1.[OH-].[Li+].Cl>O>[NH:3]1[CH:4]=[CH:5][N:1]=[C:2]1[NH:6][C:7]([CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH:18]=2)[CH:13]=[N:12]1)=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium Hydroxide2×HCID 8028TetrahydrofuranHCID 10592298HCID 10592298, compound

Product 1

HCID 19085003HCID 19085003, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the product of Example 1327b Part C (145 mg, 443 μmol), tetrahydrofuran (2 mL) and water (2 mL) was treated with aqueous lithium hydroxide (1.0 M; 0.56 mL, 560 μmol) and stirred at room temperature for 21 h. The reaction was incomplete by thin-layer chromatography, so additional lithium hydroxide solution (a total of 1.35 mL) was added in four portions over the next 8 h. After stirring for 16 h more, the reaction was acidified with aqueous hydrochloric acid (1.0M) and concentrated under vacuum. The residue was partitioned between water and dichloromethane, and the organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated to provide the title product (49 mg, 37%): 1H NMR (DMSO-d6) δ 8.41 (s, 1H), 8.24 (s, 1H), 7.94 (d, 1H), 7.76 (d, 1H), 6.67 (s, 2H), 4.73 (t, 2H), 3.00 (t, 2H); High resolution mass spectrum (NH3 --CI) calculated (M+H+) 300.1097, found 300.1097.

Workup

  1. additionwas added in four portions over the next 8 h
  2. stirringAfter stirring for 16 h more
  3. concentrationconcentrated under vacuum
  4. customThe residue was partitioned between water and dichloromethane
  5. dry with materialthe organic phase was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7c72dbcad7774b77a494779b82e38d02
Source dataset
uspto-grants-1998_06
Patent number
US05760028

Reaction notes

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