Hydrochloric Acid → HCID 59662189, compound

HRID 409570Notes

Reaction equation

HRID 409570 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][N:19]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[O:22][CH2:21][C:20]2=[O:29])[CH2:13][CH2:12]1.[OH-].[Na+].Cl>CO>[Cl:10][C:8]1[CH:7]=[CH:6][C:5]([CH:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][N:19]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[O:22][CH2:21][C:20]3=[O:29])[CH2:13][CH2:12]2)=[C:4]([CH:9]=1)[C:3]([OH:30])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24804650HCID 24804650, compound

Product 1

HCID 59662189HCID 59662189, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 4-6 (1.00 g, 2.33 mmol) was dissolved in methanol (3 mL), treated with 3N sodium hydroxide solution (3.1 mL, 9.33 mmol) at rt, and stirred for 24 hrs. The reaction was neutralized with 2N hydrochloric acid solution (7 mL, 14 mmol) and purified by RP HPLC (gradient elution with 15-90% acetonitrile in water, each containing 0.1% TFA). Lyophilization afforded product Compound 4-7 as a white solid (trifluoroacetate salt, 0.62 g, 64%). 1H NMR (300 MHz, DMSO) δ 7.76 (br s, 1H), 7.64 (br d, J=8 Hz, 1H), 7.41 (d, J=8.5 Hz, 1H), 7.30 (d, J=6.9 Hz, 1H), 7.11-7.06 (m, 3H), 4.70 (s, 2H), 4.33 (m, 2H), 3.86-3.20 (m, 7H), 2.04-1.86 (m, 4H); MS (ES+) m/z 414.9 (M+1); Anal Calcd. for C22H23ClN2O4-1.75CF3CO2H: C, 50.05; H, 4.08; N, 4.60. Found: C, 50.11; H, 4.23; N, 4.56.

Workup

  1. custompurified by RP HPLC (
  2. washgradient elution with 15-90% acetonitrile in water

Sources & evidence

ORD record
ord-c0376ecd7c184d12a2196ff1f6fbb835
Source dataset
uspto-grants-2014_06
Patent number
US08759342B2

Reaction notes

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