Dimethylformamide → HCID 21921297, compound

HRID 2373778Notes

Reaction equation

HRID 2373778 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[C:5](=[CH:7][CH:8]=[CH:9][C:10]=2C(O)=O)[CH:6]=1.[Br:14][C:15]1[CH:23]=[CH:22][C:18]([CH2:19][CH2:20][NH2:21])=[CH:17][CH:16]=1.CC(C)N=C=NC(C)C.C1C=CC2N([OH:42])N=NC=2C=1.CN([CH:46]=[O:47])C>CN(C1C=CN=CC=1)C>[Br:14][C:15]1[CH:23]=[CH:22][C:18]([CH2:19][CH2:20][NH:21][C:46]([C:2]2[C:1]([OH:42])=[CH:6][C:5]3[C:4](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=2)=[O:47])=[CH:17][CH:16]=1

Participants

7

Reactant 5

HCID 6228Dimethylformamide2×HCID 68471-Naphthoic acidHCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 533915p-Bromophenethylamine

Product 1

HCID 21921297HCID 21921297, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To 1.0 g (2.5 mmol) of resin-bound naphthoic acid was added a mixture of 1.5 g (7.5 mmol) of 4-Bromophenethylamine, 7.5 mL (7.5 mmol) of 1.0 M DIC in DMF, 7.5 mL (7.5 mmol) of 1.0 M HOBt in DMF, and a catalytic amount of DMAP. The resulting mixture was left on a shaker overnight. The resin was washed with DMF, MeOH, DCM three times of each to give resin-bound N-2-(4-Bromophenyl)ethyl-3-hydroxyl-2-naphthamide.

Workup

  1. washThe resin was washed with DMF, MeOH, DCM three times of

Sources & evidence

ORD record
ord-d42a47e9470c4c06baac94fe9ebda4b9
Source dataset
uspto-grants-2008_12
Patent number
US07459472B2

Reaction notes

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