N,N-Dimethylethylenediamine → HCID 45139070, compound

HRID 2061001Notes

Reaction equation

HRID 2061001 reaction equation
[CH3:1][O:2][C:3]1[C:15]2[NH:14][C:13]3[C:8](=[CH:9][C:10]([C:16]([OH:18])=O)=[CH:11][CH:12]=3)[C:7]=2[CH:6]=[C:5]2[C:19]3[CH:20]=[C:21]([C:26]([OH:28])=O)[CH:22]=[CH:23][C:24]=3[NH:25][C:4]=12.F[P-](F)(F)(F)(F)F.[N:36]1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.[CH3:62][N:63]([CH3:67])[CH2:64][CH2:65][NH2:66].[CH:68]([N:71]([CH2:75]C)[CH:72](C)C)(C)[CH3:69]>CN(C=O)C>[CH3:62][N:63]([CH3:67])[CH2:64][CH2:65][NH:66][C:26]([C:21]1[CH:20]=[C:19]2[C:24](=[CH:23][CH:22]=1)[NH:25][C:4]1[C:3]([O:2][CH3:1])=[C:15]3[NH:14][C:13]4[CH:12]=[CH:11][C:10]([C:16]([NH:36][CH2:69][CH2:68][N:71]([CH3:75])[CH3:72])=[O:18])=[CH:9][C:8]=4[C:7]3=[CH:6][C:5]2=1)=[O:28]

Participants

6

Reactant 4

HCID 66053N,N-DimethylethylenediamineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 22025395HCID 22025395, compound

Product 1

HCID 45139070HCID 45139070, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-methoxy-5,7-dihydroindolo[2,3-b]carbazole-2,10-dicarboxylic acid (467.7 mg, 1.27 mmol), benzotriazol-1-yloxy-tripyrrolidinophosphonium hexafluorophosphate (1.458 g, 2.80 mmol), N,N-dimethylethylenediamine (0.31 mL, 2.80 mmol) and N,N-diisopropylethylamine (1.33 mL, 7.64 mmol) in anhydrous DMF (25 mL) was stirred at room temperature overnight. The solvent and DIEA were removed under vacuum. The residue was subjected to flash chromatography to provide the title product (0.498 g, 76%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 11.54 (s, 2H), 8.71 (d, J=1.2 Hz, 2H), 8.62 (s, 1H), 8.32 (t, J=6.4 Hz, 2H), 7.88 (dd, J=8.4, 2.0 Hz, 2H), 7.48 (d, J=8.4 Hz, 2H), 4.12 (s, 3H), 3.42 (q, J=6.4 Hz, 4H), 3.05-2.96 (m, 4H), 2.21 (s, 12H); MS (ESI) m/z 513.3 (M−H)−; MS (ESI) m/z 515.1 (M+H)+

Workup

  1. customThe solvent and DIEA were removed under vacuum

Sources & evidence

ORD record
ord-f37760c9182b475da1a763c513947b93
Source dataset
uspto-grants-2012_10
Patent number
US08278341B2

Reaction notes

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