3-Chlorophenylacetic acid → HCID 59395618, compound

HRID 1097673Notes

Reaction equation

HRID 1097673 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:6][CH:7]=1.Cl.CN(C)CCCN=C=NCC.N1(O)C2C=CC=CC=2N=N1.[CH2:34]([N:38]1[C:46]2[N:45]=[C:44]([Cl:47])[NH:43][C:42]=2[C:41](=[O:48])[N:40]([CH2:49][CH2:50][CH2:51]/[C:52](=[N:55]/[H])/[NH:53]O)[C:39]1=[O:57])[CH2:35][CH2:36][CH3:37]>CN1CCCC1=O>[CH2:34]([N:38]1[C:46]2[N:45]=[C:44]([Cl:47])[NH:43][C:42]=2[C:41](=[O:48])[N:40]([CH2:49][CH2:50][CH2:51][C:52]2[N:53]=[C:9]([CH2:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[O:11][N:55]=2)[C:39]1=[O:57])[CH2:35][CH2:36][CH3:37]

Participants

6

Reactant 4

HCID 158793-Chlorophenylacetic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178506474HCID 178506474, compound

Product 1

HCID 59395618HCID 59395618, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

(3-Chlorophenyl)acetic acid (0.1 mmol), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (21 mg, 0.11 mmol) and 1H-1,2,3-benzotriazol-1-ol (15 mg, 0.11 mmol) were stirred in 1-methyl-2-pyrrolidinone (1 ml). To this was added (1Z)-4-(3-butyl-8-chloro-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)-N-hydroxybutanimidamide (34 mg, 0.1 mmol) and the mixture stirred at rt for 17 h and then at 80° C. for 24 h. The reaction mixture was purified, without further modification, by preparative HPLC (auto prep) to give the title compound (13 mg, 27%).

Workup

  1. waitat 80° C. for 24 h
  2. customThe reaction mixture was purified, without further modification, by preparative HPLC (auto prep)

Sources & evidence

ORD record
ord-05f2dadf165c4731be3933f29fbf22ea
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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