Diisopropylcarbodiimide → HCID 21921219, compound

HRID 1245083Notes

Reaction equation

HRID 1245083 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20])[O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=O)=[CH:8][CH:7]=1.[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][N:24]=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:29][C:26]1[CH:27]=[CH:28][C:23]([NH:22][C:13](=[O:15])[CH2:12][C:9]2[CH:8]=[CH:7][C:6]([O:5][C:4]3[CH:16]=[CH:17][C:18]([N+:19]([O-:21])=[O:20])=[C:2]([OH:1])[CH:3]=3)=[CH:11][CH:10]=2)=[N:24][CH:25]=1

Participants

7

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 706222-Amino-5-bromopyridineHCID 757711-HydroxybenzotriazoleHCID 21921907HCID 21921907, compound

Product 1

HCID 21921219HCID 21921219, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×

Procedure

To 3.0 g (2.5 mmol) of above resin-bound [4-(3-hydroxy-4-nitro-phenoxy)-phenyl]-acetic acid were added 1.30 g (7.5 mmol) of 2-amino-5-bromopyridine, 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 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-(5-bromo-pyridin-2-yl)-2-[4-(3-hydroxy-4-nitro-phenoxy)-phenyl]-acetamide

Workup

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

Sources & evidence

ORD record
ord-2338b9cc945647cf8ac23ef51502b148
Source dataset
uspto-grants-2006_10
Patent number
US07122580B2

Reaction notes

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