HCID 10488759, compound → HCID 21191337, compound

HRID 1069113Notes

Reaction equation

HRID 1069113 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][CH:15]=1)/[CH:8]=[CH:9]/[C:10]([OH:12])=O)(=[O:3])[CH3:2].[Cl:16][CH2:17][CH:18]1[C:26]2[C:21](=[CH:22][C:23]([N+:27]([O-:29])=[O:28])=[CH:24][CH:25]=2)[NH:20][CH2:19]1>>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][CH:15]=1)/[CH:8]=[CH:9]/[C:10]([N:20]1[C:21]2[C:26](=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=2)[CH:18]([CH2:17][Cl:16])[CH2:19]1)=[O:12])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 10488759HCID 10488759, compoundHCID 15023502HCID 15023502, compound

Product 1

HCID 21191337HCID 21191337, compoundYield 80%

Procedure

Similar reaction of (E)-3-(acetylamino)cinnamic acid and crude 3-chloromethyl-6-nitroindoline (6) (prepared as in Example 2) gave a crude product which was recrystallised from DMF/MeOH/H2O to give 1-[(E)-3-(acetylamino)cinnamoyl]-3-chloromethyl-6-nitroindoline (13) (80%), mp 229-230° C. 1H NMR [(CD3)2SO] δ10.06 (s, 1 H, NH), 8.97 (s, 1 H, H-7), 7.99 (dd, J=8.3, 2.3 Hz, 1 H, H-5), 7.86 (s, 1 H, H-2), 7.73-7.61 (m, 2 H, H-4,4′), 7.66 (d, J=15.3 Hz, 1 H, PhCH═CH), 7.53 (d, J=7.8 Hz, 1 H, H-6), 7.38 (t, J=7.9 Hz, 1 H, H-5), 7.08 (d, J=15.4 Hz, 1 H, PhCH═CH), 4.65 (t, J 10.0 Hz, 1 H, H-2), 4.33 (dd, J=10.7, 5.2 Hz, 1 H, H-2), 4.14-4.00 (m, 3 H, H-3, CH2Cl ), 2.07 (s, 3 H, CH3).

Workup

  1. customgave a crude product which
  2. customwas recrystallised from DMF/MeOH/H2O

Sources & evidence

ORD record
ord-189ece22bc7a4dbe8c8b03d766d34250
Source dataset
uspto-grants-2001_06
Patent number
US06251933B1

Reaction notes

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