Benzylamine → HCID 178487783, compound

HRID 321960Notes

Reaction equation

HRID 321960 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]2[N:6]=[C:7]([C:9]3[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=3)[NH:8][C:4]=2[C:3]=1[CH2:23][C:24]([OH:26])=O.Cl.CN(C)CCCN=C=NCC.[CH2:39]([NH2:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>CC(N(C)C)=O>[F:1][C:2]1[CH:22]=[CH:21][C:5]2[N:6]=[C:7]([C:9]3[CH:10]=[C:11]([O:19][CH3:20])[C:12]([O:17][CH3:18])=[C:13]([O:15][CH3:16])[CH:14]=3)[NH:8][C:4]=2[C:3]=1[CH2:23][C:24]([NH:46][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:26]

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178487784HCID 178487784, compound

Product 1

HCID 178487783HCID 178487783, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 2-[5-fluoro-2-(3,4,5-trimethoxyphenyl)benzimidazolyl]acetic acid (1.8 mmole, 650 mg) in DMA (5 ml), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide HCl (2.7 mmole, 0.52 g) and benzylamine (2.52 mmole, 0.28 ml) is stirred at room temperature for 22 hours. The reaction mixture is added dropwise onto ice (50 g), and the precipitate is filtered off and dried in vacuo (R1=(CH2)x—C(O)—NH—(CH2)y—R5, x=1, R5=phenyl, R2=3,4,5-trimethoxy-phenyl, R3=F, n=1, y=1).

Workup

  1. additionThe reaction mixture is added dropwise onto ice (50 g)
  2. filtrationthe precipitate is filtered off
  3. dry with materialdried in vacuo (R1=(CH2)x—C(O)—NH—(CH2)y—R5, x=1, R5=phenyl, R2=3,4,5-trimethoxy-phenyl, R3=F, n=1, y=1)

Sources & evidence

ORD record
ord-1b169cbbec754528a127ac7951509747
Source dataset
uspto-grants-2001_04
Patent number
US06211177B1

Reaction notes

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