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

HRID 1815210
Notes
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Reaction equation

HRID 1815210 reaction equation
C(OC([N:8]1[CH2:17][C:16]([CH3:19])([CH3:18])[C:15]2[C:10](=[CH:11][C:12]([NH:20][C:21]([C:23]3[C:24]([NH:29][CH2:30][C:31]4[CH:36]=[CH:35][N:34]=[C:33]5[NH:37][CH2:38][CH2:39][C:32]=45)=[N:25][CH:26]=[CH:27][CH:28]=3)=[O:22])=[CH:13][CH:14]=2)[CH2:9]1)=O)(C)(C)C.Cl.C([O-])(O)=O.[Na+]>O1CCOCC1>[NH:37]1[C:33]2=[N:34][CH:35]=[CH:36][C:31]([CH2:30][NH:29][C:24]3[N:25]=[CH:26][CH:27]=[CH:28][C:23]=3[C:21]([NH:20][C:12]3[CH:11]=[C:10]4[C:15]([C:16]([CH3:19])([CH3:18])[CH2:17][NH:8][CH2:9]4)=[CH:14][CH:13]=3)=[O:22])=[C:32]2[CH2:39][CH2:38]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 20773481tert-Butyl 7-[({2-[(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)amino]pyridin-3-yl}carbonyl)amino]-4,4-dimethyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 103878712-[(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)-amino]-N-(4,4-dimethyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-nicotinamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 7-({2-[(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)-amino]-pyridine-3-carbonyl}-amino)-4,4-dimethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (0.070 g), HCl (4N, 3.0 mL) and dioxane (4.0 mL) was stirred at RT for overnight. Sat'd NaHCO3 was added until the bubbling stopped. The aqueous phase was extracted with CH2Cl2 3 times. The combined organic phases were dried over Na2SO4 and evaporated to yield a tan colored residue as a crude product, which was chromatographed through HPLC. The fractions were collected and the solvent was evaporated. The residue was treated with NaHCO3 and the solvent was evaporated. The residue was washed with H2O to remove any inorganics to afford 2-[(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)-amino]-N-(4,4-dimethyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-nicotinamide. MS: (ES+) 429 (M+H). Calc'd. for C25H28N6O—428.54.

Workup

  1. extractionThe aqueous phase was extracted with CH2Cl2 3 times
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. customevaporated
  4. customto yield a tan colored residue as a crude product, which
  5. customwas chromatographed through HPLC
  6. customThe fractions were collected
  7. customthe solvent was evaporated
  8. additionThe residue was treated with NaHCO3
  9. customthe solvent was evaporated
  10. washThe residue was washed with H2O
  11. customto remove any inorganics

Sources & evidence

ORD record
ord-d5fe437074a74953a459652d6a65a222
Source dataset
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06878714B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes