2-Aminocarbonylamino-6-[4-(2-tert-butoxycarbonylaminoethyl)phenyl]indole-3-c arboxamide → 2-Aminocarbonylamino-6-[4-(2-aminoethyl)phenyl]indole-3-carboxamide hydrochloride

HRID 216628Notes

Reaction equation

HRID 216628 reaction equation
O1CCOCC1.[Cl-:7].[NH2:8][C:9]([NH:11][C:12]1[NH:13][C:14]2[C:19]([C:20]=1[C:21]([NH2:23])=[O:22])=[CH:18][CH:17]=[C:16]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][NH:32]C(OC(C)(C)C)=O)=[CH:26][CH:25]=1)[CH:15]=2)=[O:10]>>[ClH:7].[NH2:8][C:9]([NH:11][C:12]1[NH:13][C:14]2[C:19]([C:20]=1[C:21]([NH2:23])=[O:22])=[CH:18][CH:17]=[C:16]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][NH2:32])=[CH:26][CH:25]=1)[CH:15]=2)=[O:10]

Participants

3

Reactant 2

HCID 591897762-Aminocarbonylamino-6-[4-(2-tert-butoxycarbonylaminoethyl)phenyl]indole-3-c arboxamide2×HCID 86639075HCID 86639075, compound

Product 1

HCID 685532972-Aminocarbonylamino-6-[4-(2-aminoethyl)phenyl]indole-3-carboxamide hydrochloride

Procedure

4 N Hydrogene chloride dioxane solution (15 mL) was added to 2-aminocarbonylamino-6-[4-(2-tert-butoxycarbonylaminoethyl)phenyl]indole-3-c arboxamide (Compound 7-33, 65 mg, 0.15 mmol) under ice-cooling, and the mixture was stirred at room temperature overnight. After the reaction mixture was concentrated under reduced pressure, the precipitated solid was washed with ethyl acetate (3 mL), and dried under reduced pressure to give the title compound (56 mg) quantitatively as a slightly yellow solid.

Workup

  1. temperaturecooling
  2. concentrationAfter the reaction mixture was concentrated under reduced pressure
  3. washthe precipitated solid was washed with ethyl acetate (3 mL)
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-b9410f550eef47219f19216039a471cb
Source dataset
uspto-grants-2012_06
Patent number
US08193237B2

Reaction notes

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