Hydrochloric Acid → Hydrochloric Acid

HRID 2370622Notes

Reaction equation

HRID 2370622 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[C:11](=[N:12][C:13](S(C)=O)=[N:14][CH:15]=2)[N:10]2[CH:22]=[CH:23][N:24]=[C:9]12.[NH2:25][C:26]1[CH:38]=[CH:37][C:29]([C:30]([O:32]C(C)(C)C)=[O:31])=[CH:28][CH:27]=1.[ClH:39]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[C:11](=[N:12][C:13]([NH:25][C:26]3[CH:38]=[CH:37][C:29]([C:30]([OH:32])=[O:31])=[CH:28][CH:27]=3)=[N:14][CH:15]=2)[N:10]2[CH:22]=[CH:23][N:24]=[C:9]12.[ClH:39]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 233272Benzoic acid, 4-amino-, 1,1-dimethylethyl esterHCID 681947574-(2-Chloro-phenyl)-8-methanesulfinyl-4H-3,4,7,9,9b-pentaaza-cyclopenta[a]naphthalen-5-one

Product 2

HCID 313Hydrochloric AcidHCID 601685984-[4-(2-Chloro-phenyl)-5-oxo-4,5-dihydro-3,4,7,9,9b-pentaaza-cyclopent a[a]naphthalen-8-ylamino]-benzoic acid

Procedure

A mixture of Example 1E (200.0 mg, 0.556 mmol), tert-butyl 4-aminobenzoate (129 mg, 0.667 mmol), and concentrated HCl (0.08 mL, 2.63 mmol) was heated at 160° C. for 30 minutes in a Biotage microwave reactor. The solvent was decanted. The remaining residue was treated with water, sonicated, filtered, washed with water, and oven-dried to provide the title compound as an HCl salt.

Workup

  1. customThe solvent was decanted
  2. additionThe remaining residue was treated with water
  3. customsonicated
  4. filtrationfiltered
  5. washwashed with water
  6. customoven-dried

Sources & evidence

ORD record
ord-e4b94cb890564f7fb0b17b3aa1febf74
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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