HCID 66697404, compound → HCID 66697493, compound

HRID 539935Notes

Reaction equation

HRID 539935 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][C:12]([C@@H:14]3[CH2:18][CH2:17][CH2:16][N:15]3[C:19](=[O:27])[CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:13])[CH:9]=2)[NH:4][C:3]=1[C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:35]([C@@H:37]2[CH2:41][CH2:40][CH2:39][N:38]2[C:42](=[O:50])[CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[O:36])=[CH:30][CH:29]=1.[C:51]([Cu])#[N:52]>CN(C=O)C>[C:51]([C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][C:12]([C@@H:14]3[CH2:18][CH2:17][CH2:16][N:15]3[C:19](=[O:27])[CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:13])[CH:9]=2)[NH:4][C:3]=1[C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:35]([C@@H:37]2[CH2:41][CH2:40][CH2:39][N:38]2[C:42](=[O:50])[CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[O:36])=[CH:30][CH:29]=1)#[N:52]

Participants

4

Reactant 2

HCID 66697404HCID 66697404, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 66697493HCID 66697493, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the bromo compound from Example 126 (150 mg, 0.2 mmol), CuCN (50 mg, 0.6 mmol) and DMF (3 mL) was refluxed under N2 protection overnight. The mixture was purified by RPLC to afford the product. MS (ESI) m/e (M+H+): 679. 1H NMR (CDCl3) δ: 7.73-7.70 (m, 4H), 7.38-7.29 (m, 4H), 7.21-7.04 (m, 6H), 4.63-4.60 (m, 1H), 4.49-4.47 (m, 1H), 3.81-3.59 (m, 4H), 2.48-1.97 (m, 8H).

Workup

  1. temperaturewas refluxed under N2 protection overnight
  2. customThe mixture was purified by RPLC
  3. customto afford the product

Sources & evidence

ORD record
ord-a2127cf312aa4931a2a9ef5772ef1693
Source dataset
uspto-grants-2014_10
Patent number
US08871759B2

Reaction notes

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