Dimethylformamide → HCID 10116186, compound

HRID 2117291Notes

Reaction equation

HRID 2117291 reaction equation
C(OC(=O)[N:7]([CH2:17][CH:18]([OH:41])[CH:19]([NH:29]C(=O)CNC(=O)CCCCBr)[CH2:20][C:21]1[CH:26]=[C:25]([OH:27])[CH:24]=[C:23]([F:28])[CH:22]=1)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH3:16])[CH:10]=1)(C)(C)C.[C:43]([O-:46])([O-])=O.[Cs+].[Cs+].[CH3:49][N:50]([CH:52]=[O:53])C>>[CH2:15]([C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[CH2:8][NH:7][CH2:17][CH:18]([CH:19]1[CH2:20][C:21]2=[CH:26][C:25](=[CH:24][C:23]([F:28])=[CH:22]2)[O:27][CH2:11][CH2:10][CH2:9][CH2:8][C:52](=[O:53])[NH:50][CH2:49][C:43](=[O:46])[NH:29]1)[OH:41])[CH3:16]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 11273779HCID 11273779, compound

Product 1

HCID 10116186HCID 10116186, compoundYield 25%

Procedure

To a solution of the product from Step 6 (78 mg, 0.12 mmol, 1.00 eq.) and anhydrous DMF (1 mL) is added Cs2CO3 (flame-dried, 78 mg, 0.24 mmol, 2.00 eq.) under N2 with stirring overnight. The reaction mixture is filtered through Celite and then concentrated in vacuo. The crude product is then stirred with Dowex 50WX2-400 ion-exchange resin at 60° C. for 2 hours. The product is released from resin with 7N NH3/MeOH through a frit and the filtrate is concentrated in vacuo, yielding the final product as a white solid (14 mg, 25% yield). Calculate accurate mass for C26H34BrFN3O4+H1: 472.2611. Accurate Mass found for C26H34BrFN3O4+H1: 472.2592.

Workup

  1. filtrationThe reaction mixture is filtered through Celite
  2. concentrationconcentrated in vacuo
  3. stirringThe crude product is then stirred with Dowex 50WX2-400 ion-exchange resin at 60° C. for 2 hours
  4. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-2a64233c1db24c818edc3fa53d4054f6
Source dataset
uspto-grants-2008_10
Patent number
US07442691B2

Reaction notes

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