Diisopropylethylamine → N-(4,4-Dimethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-2[(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-amino]-benzamide

HRID 969680Notes

Reaction equation

HRID 969680 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH2:10][NH:11][C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14]([OH:16])=O)=[CH:2]1.[NH2:21][C:22]1[CH:31]=[C:30]2[C:25]([C:26]([CH3:34])([CH3:33])[CH2:27][C:28](=[O:32])[NH:29]2)=[CH:24][CH:23]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH3:33][C:26]1([CH3:34])[C:25]2[C:30](=[CH:31][C:22]([NH:21][C:14](=[O:16])[C:13]3[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=3[NH:11][CH2:10][C:3]3[C:4]4[C:5](=[N:6][CH:7]=[CH:8][CH:9]=4)[NH:1][CH:2]=3)=[CH:23][CH:24]=2)[NH:29][C:28](=[O:32])[CH2:27]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 144764787-Amino-4,4-dimethyl-3,4-dihydroquinolin-2(1H)-oneHCID 664154252-[(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-amino]-benzoic acid

Product 1

HCID 10071896N-(4,4-Dimethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-2[(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-amino]-benzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-[(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-amino]-benzoic acid (Step A, Example 113) (200 mg), 7-amino-4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one (143 mg), TBTU (265 mg), and DIEA (0.14 mL) in DMF (2 mL) was stirred at RT under N2 atmosphere for 16 h. The mixture was diluted with EtOAc (10 mL) and extracted with water (2×15 mL). The organic layer was dried over Na2SO4 and the crude material was purified by flash chromatography (SiO2, 5% MeOH/CH2Cl2) to afford the titled compound as a white solid. MS (ES+): 440.0 (M+H)+. Calc'd for C26H25N5O2-439.52.

Workup

  1. extractionextracted with water (2×15 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customthe crude material was purified by flash chromatography (SiO2, 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-2151affb0ee44aa2a655bbad3c311d1a
Source dataset
uspto-grants-2007_12
Patent number
US07307088B2

Reaction notes

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