O-Phenylenediamine → HCID 85417831, compound

HRID 346874Notes

Reaction equation

HRID 346874 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH:11]=[N:12][O:13][CH2:14][C:15]3[S:19][C:18]([C:20]([OH:22])=O)=[CH:17][CH:16]=3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.O[N:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[N:26]=N1.CN(C)CCCN=C=NCC.C(N(CC)CC)C.C1(N)C=CC=CC=1N>ClCCl>[NH2:24][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[NH:26][C:20]([C:18]1[S:19][C:15]([CH2:14][O:13][N:12]=[CH:11][C:9]2[CH:8]=[CH:7][C:6]3[O:1][CH2:2][CH2:3][O:4][C:5]=3[CH:10]=2)=[CH:16][CH:17]=1)=[O:22]

Participants

7

Reactant 5

HCID 7243O-PhenylenediamineHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 86594824HCID 86594824, compound

Product 1

HCID 85417831HCID 85417831, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 100 mg (0.31 mmol) 5-(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyleneaminooxymethyl)-thiophene-2-carboxylic acid, 65 mg (0.47 mmol) 1-hydroxybenzotriazol, 92 mg (0.47 mmol) N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide and 65 μl (0.47 mmol) triethylamine in 3 ml dichloromethane was stirred for 15 minutes. After addition of 68 mg (0.63 mmol) phenylenediamine the reaction mixture was stirred overnight. The solvent was evaporated and the residue was subjected to preparative HPLC to yield 88 mg (0.21 mmol) 5-(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyleneaminooxymethyl)-thiophene-2-carboxylic acid (2-amino-phenyl)-amide (17); exact MW [M+H] calc'd: 410.12; MW found [M+H]: 410.2. 1H-NMR (400 MHz, (CH3)2SO): δ=9.67 (s, 1H), 8.18 (s, 1H), 7.85 (m, 1H), 7.20 (m, 1H), 7.14–7.09 (m, 3H), 6.97 (m, 1H), 6.91 (m, 1H), 6.77 (m, 1H), 6.58 (m, 1H), 5.29 (s, 2H), 4.90 (s, 2H), 4.26 (m, 4H)

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-f9d01c8d1db44ebab52347e23261b5fb
Source dataset
uspto-grants-2007_02
Patent number
US07173060B2

Reaction notes

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