N,N-Dimethylethylenediamine → HCID 60164658, compound

HRID 513706Notes

Reaction equation

HRID 513706 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([CH:11]2[C:24]3[CH:23]=[CH:22][C:21]4[C:16](=[N:17][CH:18]=[CH:19][CH:20]=4)[C:15]=3[NH:14][S:13](=[O:26])(=[O:25])[N:12]2[CH3:27])=[CH:7][C:3]=1[C:4](O)=[O:5].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:50][N:51]([CH3:55])[CH2:52][CH2:53][NH2:54].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:50][N:51]([CH3:55])[CH2:52][CH2:53][NH:54][C:4](=[O:5])[C:3]1[CH:7]=[C:8]([CH:11]2[C:24]3[CH:23]=[CH:22][C:21]4[C:16](=[N:17][CH:18]=[CH:19][CH:20]=4)[C:15]=3[NH:14][S:13](=[O:26])(=[O:25])[N:12]2[CH3:27])[CH:9]=[CH:10][C:2]=1[F:1]

Participants

6

Reactant 4

HCID 66053N,N-DimethylethylenediamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68183192HCID 68183192, compound

Product 1

HCID 60164658HCID 60164658, compoundYield 14.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a similar fashion, using route 37 general procedure 90, 2-fluoro-5-(2-methyl-3,3-dioxo-1,2,3,4-tetrahydro-3λ*6*-thia-2,4,5-triaza-phenanthren-1-yl)-benzoic acid 424 (60 mg, 0.15 mmol), TBTU (50 mg, 0.15 mmol), N,N-dimethylethane-1,2-diamine (16.9 μl, 0.15 mmol) and DIPEA (25.6 μl, 0.15 mmol) in DCM (1 ml) gave the title compound (10 mg, 14%) after purification by preparative HPLC (acidic conditions 1).

Sources & evidence

ORD record
ord-f7d8b8d01193421f8292373939d3919b
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…