N,N-Dimethylethylenediamine → HCID 45139070, compound

HRID 1949130Notes

Reaction equation

HRID 1949130 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, 2 H), 8.71 (d, J=1.2 Hz, 2H), 8.62 (s, 1 H), 8.32 (t, J=6.4 Hz, 2 H), 7.88 (dd, J=8.4, 2.0 Hz, 2 H), 7.48 (d, J=8.4 Hz, 2 H), 4.12 (s, 3 H), 3.42 (q, J=6.4 Hz, 4 H), 3.05-2.96 (m, 4 H), 2.21 (s, 12 H); 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-ba15aa4fc56141ad8338be6a9029277d
Source dataset
uspto-grants-2013_03
Patent number
US08399502B2

Reaction notes

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