N,N-Dimethylethylenediamine → HCID 71534653, compound

HRID 1519306Notes

Reaction equation

HRID 1519306 reaction equation
C[O:2][C:3]([C:5]1[C:6]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([OH:32])=O)=[CH:26][CH:25]=2)=[CH:7][CH:8]=[C:9]([C:11]2[S:12][CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=3)[N:15]=2)[CH:10]=1)=[O:4].[CH3:33][N:34]([CH3:38])[CH2:35][CH2:36][NH2:37]>>[Cl:23][C:18]1[CH:17]=[C:16]([C:14]2[N:15]=[C:11]([C:9]3[CH:10]=[C:5]([C:3]([OH:2])=[O:4])[C:6]([C:24]4[CH:29]=[CH:28][C:27]([C:30](=[O:32])[NH:37][CH2:36][CH2:35][N:34]([CH3:38])[CH3:33])=[CH:26][CH:25]=4)=[CH:7][CH:8]=3)[S:12][CH:13]=2)[CH:21]=[CH:20][C:19]=1[Cl:22]

Participants

3

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 86679835HCID 86679835, compound2×

Product 1

HCID 71534653HCID 71534653, compoundYield 73%

Procedure

Using the conditions of General Procedure E for Amide Coupling in Parallel Mode, 4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2,4′-dicarboxylic acid 2-methyl ester (which may be prepared as described for Intermediate 8; 100 mg, 0.21 mmol) was reacted with N,N-dimethylethylenediamine (available from Aldrich Chemical Company, Inc.; 55 mg, 0.62 mmol). The resulting ester was hydrolyzed and the acid was purified using HPLC Purification Conditions B to give 4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-4′-(2-dimethylamino-ethylcarbamoyl)-biphenyl-2-carboxylic acid (81 mg, 73%). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.73 (t, J=5.4 Hz, 1H), 8.47 (s, 1H), 8.41 (d, J=2.0 Hz, 1H), 8.33 (d, J=2.0 Hz, 1H), 8.25 (dd, J=8.0, 1.8 Hz, 1H), 8.09 (dd, J=8.5, 2.0 Hz, 1H), 7.93 (d, J=8.3 Hz, 2H), 7.77 (d, J=8.5 Hz, 1H), 7.58 (d, J=8.0 Hz, 1H), 7.52 (d, J=8.3 Hz, 2H), 3.63 (q, J=5.8 Hz, 2H), 3.22-3.27 (m, 2H), 2.84 (s, 6H).

Workup

  1. customthe acid was purified
  2. customHPLC Purification Conditions B

Sources & evidence

ORD record
ord-dce93ad5a0ca42e080c3ac2657306d4e
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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