Hydrochloric Acid → N-(4,4-Dimethyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-2-[(1H-pyrrolo[2,3-b]pyridin-6-ylmethyl)-amino]-nicotinamide

HRID 888136Notes

Reaction equation

HRID 888136 reaction equation
C([N:4]1[CH2:13][C:12]([CH3:15])([CH3:14])[C:11]2[C:6](=[CH:7][C:8]([NH:16][C:17](=[O:35])[C:18]3[CH:23]=[CH:22][CH:21]=[N:20][C:19]=3[NH:24][CH2:25][C:26]3[N:31]=[C:30]4[NH:32][CH:33]=[CH:34][C:29]4=[CH:28][CH:27]=3)=[CH:9][CH:10]=2)[CH2:5]1)(=O)C.Cl.C([O-])(O)=O.[Na+]>CCO>[CH3:14][C:12]1([CH3:15])[C:11]2[C:6](=[CH:7][C:8]([NH:16][C:17](=[O:35])[C:18]3[CH:23]=[CH:22][CH:21]=[N:20][C:19]=3[NH:24][CH2:25][C:26]3[N:31]=[C:30]4[NH:32][CH:33]=[CH:34][C:29]4=[CH:28][CH:27]=3)=[CH:9][CH:10]=2)[CH2:5][NH:4][CH2:13]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 16225620N-(2-Acetyl-4,4-dimethyl-1,2,3,4-tetrahydroisoquinolin-7-yl)-2-[(1H-pyrrolo[2,3-b]pyridin-6-ylmethyl)amino]nicotinamide

Product 1

HCID 16225621N-(4,4-Dimethyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-2-[(1H-pyrrolo[2,3-b]pyridin-6-ylmethyl)-amino]-nicotinamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

N-(2-Acetyl-4,4-dimethyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-2-[(1H-pyrrolo[2,3-b]pyridin-6-ylmethyl)amino]nicotinamide (0.180 g, 0.384 mmol, Example 2) was dissolved into 10 mL of EtOH and 5 mL of concentrated HCl was added. The mixture was heated to 75° C. for 4 days. The volume was reduced to ⅓. Sat'd. NaHCO3 was added until the solution became cloudy. The aqueous phase was extracted with CH2Cl2 and the combined organic phases were dried over Na2SO4, filtered and concentrated to give a brown residue. The residue was purified by HPLC (Beckman) to afford the title compound. MS (ES+): 427 (M+H). Calc'd. for C25H26N6O—426.52.

Workup

  1. additionwas added
  2. extractionThe aqueous phase was extracted with CH2Cl2
  3. dry with materialthe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a brown residue
  7. customThe residue was purified by HPLC (Beckman)

Sources & evidence

ORD record
ord-8706702f6e004f4195b213bd44be715a
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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