Dimethylamine, hydrochloride → HCID 58011934, compound

HRID 660954Notes

Reaction equation

HRID 660954 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=3)[C:17]([OH:19])=O)[C:11](=[O:23])[N:10]([CH2:24][C:25]([NH:27][C:28]([CH3:40])([C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[CH:31]=3)[CH3:29])=[O:26])[N:9]=2)=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.C[CH2:52][N:53]=[C:54]=NCCCN(C)C.Cl.Cl.CNC.C(N(CC)C(C)C)(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=3)[C:17]([N:53]([CH3:54])[CH3:52])=[O:19])[C:11](=[O:23])[N:10]([CH2:24][C:25]([NH:27][C:28]([CH3:40])([C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:37])([F:39])[F:38])[CH:31]=3)[CH3:29])=[O:26])[N:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 10473Dimethylamine, hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58012040HCID 58012040, compound

Product 1

HCID 58011934HCID 58011934, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

30 mg (0.052 mmol) of 3-(3-(4-chlorophenyl)-1-[2-(1-methyl-1-[3-(trifluoromethyl)phenyl]ethylamino)-2-oxoethyl]-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-ylmethyl)-benzoic acid (Example 471) are placed in 0.5 ml of DMF and treated with 9.2 mg (0.068 mmol) of HOBt and 13.0 mg (0.068 mmol) of EDC hydrochloride. After 10 mins' stirring, 6.0 mg (0.073 mmol) of dimethylamine hydrochloride and 10.2 mg (0.079 mmol) of N,N-diisopropylethylamine are added and the mixture is stirred overnight at RT. Without further workup, the crude product is purified directly by preparative HPLC [Method 10]. 29.8 mg (95% of theory) of the target compound are thus obtained.

Workup

  1. stirringthe mixture is stirred overnight at RT
  2. customWithout further workup, the crude product is purified directly by preparative HPLC [Method 10]
  3. custom29.8 mg (95% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-6a20133275dc43d393b8705220bbf970
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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