Acetic Acid → N-(2-Acetyl-4,4-dimethyl-1,2,3,4-tetrahydroisoquinolin-7-yl)-2-[(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)amino]nicotinamide

HRID 888142Notes

Reaction equation

HRID 888142 reaction equation
[CH3:1][C:2]1([CH3:32])[C:11]2[C:6](=[CH:7][C:8]([NH:12][C:13](=[O:31])[C:14]3[CH:19]=[CH:18][CH:17]=[N:16][C:15]=3[NH:20][CH2:21]C3N=C4NC=CC4=CC=3)=[CH:9][CH:10]=2)[CH2:5][NH:4][CH2:3]1.[CH3:33][C:34]([OH:36])=O.CN(C(O[N:45]1N=[N:52][C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][C:46]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:59]CN(C(C)C)C(C)C>CCOC(C)=O.CN(C=O)C>[C:34]([N:4]1[CH2:3][C:2]([CH3:1])([CH3:32])[C:11]2[C:6](=[CH:7][C:8]([NH:12][C:13](=[O:31])[C:14]3[CH:19]=[CH:18][CH:17]=[N:16][C:15]=3[NH:20][CH2:21][C:49]3[CH:48]=[CH:47][N:52]=[C:59]4[NH:45][CH:46]=[CH:51][C:50]=34)=[CH:9][CH:10]=2)[CH2:5]1)(=[O:36])[CH3:33]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 16225621N-(4,4-Dimethyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-2-[(1H-pyrrolo[2,3-b]pyridin-6-ylmethyl)-amino]-nicotinamide

Product 1

HCID 16224810N-(2-Acetyl-4,4-dimethyl-1,2,3,4-tetrahydroisoquinolin-7-yl)-2-[(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)amino]nicotinamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(4,4-Dimethyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-2-[(1H-pyrrolo[2,3-b]pyridin-6-ylmethyl)-amino]-nicotinamide (0.100 g, 0.235 mmol, Example 1), HOAc (Gracious, 0.025 mL, 0.42 mmol), TBTU (0.094 g, 0.293 mmol), DIEA (0.04 mL, 0.23 mmol) were dissolved into 5 mL of DMF and stirred at RT for 1 h. 50 mL of EtOAc was added and the organic phase was washed with 10% Na2CO3 and brine. Then the organic phase was dried over Na2SO4, filtered, and concentrated to give a white solid. The solid was washed with CH3CN, then purified by HPLC (Beckman) to afford the title compound. MS (ES+): 469 (M+H). Calc'd. for C27H28N6O2—468.56.

Workup

  1. washthe organic phase was washed with 10% Na2CO3 and brine
  2. dry with materialThen the organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a white solid
  6. washThe solid was washed with CH3CN
  7. custompurified by HPLC (Beckman)

Sources & evidence

ORD record
ord-8b2ddcbff23449679cd02226f914a818
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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