N,N-Diethyl-1,3-propanediamine → HCID 71534654, compound

HRID 1519304Notes

Reaction equation

HRID 1519304 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].[CH2:33]([N:35]([CH2:40][CH3:41])[CH2:36][CH2:37][CH2:38][NH2:39])[CH3:34]>>[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:39][CH2:38][CH2:37][CH2:36][N:35]([CH2:40][CH3:41])[CH2:33][CH3:34])=[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 61011N,N-Diethyl-1,3-propanediamineHCID 86679835HCID 86679835, compound2×

Product 1

HCID 71534654HCID 71534654, compoundYield 87%

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-diethyl-1,3-propanediamine (available from Aldrich Chemical Company, Inc.; 81 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′-(3-diethylamino-propylcarbamoyl)-biphenyl-2-carboxylic acid (104 mg, 87%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.63 (br s, 1H), 9.48 (br s, 1H), 1H NMR (400 MHz, DMF), d ppm 9.14 (t, J=5.6 Hz, 1H), 8.92 (s, 1H), 8.83 (d, J=1.8 Hz, 1H), 8.77 (d, J=2.0 Hz, 1H), 8.68 (dd, J=8.0, 2.0 Hz, 1H), 8.52 (dd, J=8.3, 2.0 Hz, 1H), 8.34 (d, J=8.3 Hz, 2H), 8.20 (d, J=8.5 Hz, 1H), 8.01 (d, J=8.0 Hz, 1H), 7.93 (d, J=8.0 Hz, 2H), 3.77-3.84 (m, 2H), 3.51-3.63 (m, 6H), 2.28-2.38 (m, 2H), 1.62 (t, J=7.2 Hz, 6H).

Workup

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

Sources & evidence

ORD record
ord-b32c0524998843c4812e59137d8a854c
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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