Hydrochloric Acid → HCID 117728524, compound

HRID 718573Notes

Reaction equation

HRID 718573 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([C:12]2[N:16]3[N:17]=[CH:18][CH:19]=[C:20]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[C:15]3=[N:14][C:13]=2/[CH:27]=[CH:28]/[C:29]2[CH:38]=[CH:37][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[N:30]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[Li+].[OH-].O.Cl>C1COCC1.CO>[OH:1][C:2]1[CH:11]=[C:10]([C:12]2[N:16]3[N:17]=[CH:18][CH:19]=[C:20]([N:21]4[CH2:22][CH2:23][O:24][CH2:25][CH2:26]4)[C:15]3=[N:14][C:13]=2/[CH:27]=[CH:28]/[C:29]2[CH:38]=[CH:37][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[N:30]=2)[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 117732457HCID 117732457, compound

Product 1

HCID 117728524HCID 117728524, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

Compound 6a (80 mg, 0.16 mmol) was suspended in THF/MeOH (1:1 v/v, 8 mL) and treated with 1 N LiOH solution (0.8 mL, 0.8 mmol). The mixture was stirred at 90° C. for 30 min, allowed to cool to rt, and treated with water (20 mL). The pH of the mixture was adjusted to ca. pH 3 using 1 N HCl solution. The reaction mixture was then extracted with 20% MeOH in DCM (4×200 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated to give the title compound 63 as an orange solid. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 8.60 (br. s., 1H), 8.55-8.67 (m, 1H), 8.20 (d, J=5.6 Hz, 1H), 8.12-8.18 (m, 1H), 8.04-8.12 (m, 2H), 8.00 (d, J=8.1 Hz, 1H), 7.88 (m, 3H), 7.69 (br. s., 1H), 7.37 (d, J=1.2 Hz, 1H), 7.31 (d, J=8.3 Hz, 1H), 6.49 (d, J=5.9 Hz, 1H), 4.10 (m 4H), 3.88 (m, 4H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C28H23N5O4: 494.2 (M+H). Found 494.4.

Workup

  1. temperatureto cool to rt
  2. extractionThe reaction mixture was then extracted with 20% MeOH in DCM (4×200 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-403281cd3e6e4f38bee18a58ef9ac3e9
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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