Diisopropylcarbodiimide → HCID 21921445, compound

HRID 1245079Notes

Reaction equation

HRID 1245079 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[OH:19].[Br:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28](O)=[O:29])=[CH:23][CH:22]=1.CC(C)N=C=NC(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.CN(C1C=CN=CC=1)C>[Br:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([O:8][C:9]3[CH:10]=[CH:11][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:13][CH:14]=3)=[CH:4][C:3]=2[OH:19])=[O:29])=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 74654Benzeneacetic acid, 4-bromo-HCID 757711-HydroxybenzotriazoleHCID 21921558HCID 21921558, compound

Product 1

HCID 21921445HCID 21921445, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×

Procedure

To 3.0 g (2.5 mmol) of above resin-bound 2-amino-5-(4-trifluoromethyl-phenoxy)-phenol were added 1.62 g (7.5 mmol) of 4-bromophenylacetic acid, 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 2-(4-bromo-phenyl)-N-[2-Hydroxy-4-(4-trifluoromethyl-phenoxy)-phenyl]-acetamide.

Workup

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

Sources & evidence

ORD record
ord-c16c8826cda64bf5b3c5cb32f03c5f67
Source dataset
uspto-grants-2006_10
Patent number
US07122580B2

Reaction notes

Loading…