Hydrochloric Acid → HCID 11328791, compound

HRID 425282Notes

Reaction equation

HRID 425282 reaction equation
[CH2:1]([N:3]([CH2:28][CH3:29])[C:4]([C:6]1[CH:7]=[CH:8][C:9]2[C:10](=[C:20]3[CH2:25][CH2:24][N:23]([CH:26]=S)[CH2:22][CH2:21]3)[C:11]3[C:16]([O:17][C:18]=2[CH:19]=1)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2].S(C1C=CC(C)=CC=1)(OC)(=O)=O.[NH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.Cl>C(Cl)(Cl)Cl>[CH2:1]([N:3]([CH2:28][CH3:29])[C:4]([C:6]1[CH:7]=[CH:8][C:9]2[C:10](=[C:20]3[CH2:25][CH2:24][N:23]([CH:26]=[N:42][C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[CH2:22][CH2:21]3)[C:11]3[C:16]([O:17][C:18]=2[CH:19]=1)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 6645Methyl p-toluenesulfonateHCID 11165674HCID 11165674, compound

Product 1

HCID 11328791HCID 11328791, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A sample of compound 11b (0.1 g, 0.25 mmol) in 1 mL of chloroform was placed in a pressure tube and treated with methyl tosylate (0.037 mL, 0.25 mmol). The reaction was heated for 1 h on a steam bath. At that time the reaction was cooled to room temperature and aniline (0.023 mL, 0.25 mmol) was added, and the reaction was heated again on a steam bath for another 2 h. After 2 h, the reaction was cooled, washed with 1 N NaOH, and evaporated. Flash chromatography on silica gel was used to purify the crude material, eluting the product with 5% methanol/CH2Cl2, followed by conversion to its hydrochloride salt with ethereal hydrogen chloride (0.004 g, 0.009 mmol). MS m/z (MH+) 466.3. 1H NMR 300 MHz (CDCl3) δ 1.2 (br s, 6H), 3.1 (m, 4H), 3.3 (d, 2H) 3.4-3.8 (m, 4H), 4.3 (s, 2H),) 7.1-7.4 (m, 10H), 7.7 (s, 2H), 8.0 (s, 1H), 13.6 (s, 1H).

Workup

  1. temperatureThe reaction was heated for 1 h on a steam bath
  2. temperaturethe reaction was heated again on a steam bath for another 2 h
  3. temperaturethe reaction was cooled
  4. washwashed with 1 N NaOH
  5. customevaporated
  6. customto purify the crude material
  7. washeluting the product with 5% methanol/CH2Cl2

Sources & evidence

ORD record
ord-683cfe179c464325abb48d0507a8c70c
Source dataset
uspto-grants-2012_01
Patent number
US08106207B2

Reaction notes

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