Dimethylformamide → HCID 11663953, compound

HRID 2220670Notes

Reaction equation

HRID 2220670 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[CH2:18][C:19]1[C:27]2[C:22](=[CH:23][C:24]([C:28]#[N:29])=[CH:25][CH:26]=2)[N:21]([CH2:30][CH3:31])[CH:20]=1)[C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:6].N[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36]N=1.CN1C[CH2:45][O:44]CC1.C[N:48]([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.CN([CH:77]=[O:78])C>O>[N:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:8][NH:7][C:5]([C:4]1[CH:3]=[C:2]([C:33]2[CH:36]=[CH:37][C:38]([O:78][CH3:77])=[CH:39][C:34]=2[CH2:45][OH:44])[C:17]([CH2:18][C:19]2[C:27]3[C:22](=[CH:23][C:24]([C:28](=[NH:48])[NH2:29])=[CH:25][CH:26]=3)[N:21]([CH2:30][CH3:31])[CH:20]=2)=[CH:16][CH:15]=1)=[O:6]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 195092-PyridinemethanamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 69202216HCID 69202216, compound

Product 1

HCID 11663953HCID 11663953, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Part B. 3-bromo-4-(6-cyano-1-ethyl-1H-indol-3-ylmethyl)-N-pyridin-2-ylmethyl-benzamide: A mixture of the compound of Part A (0.18 g, 0.47 mmol), 2-aminomethylpyridine (0.058 mL, 0.56 mmol), NMM (0.4 mL, 3.8 mmol) and BOP reagent (0.26 g, 0.59 mmol) in DMF (1.5 mL) was stirred overnight at rt. Reaction mixture was diluted with water and extracted with EtOAc. Organic layer was washed with brine, dried over anh. Na2SO4, filtered and evaporated. Chromatography on silica gel provided the amide product (0.2 g, 91%). LC/MS m/z 473.2, 475.2 (M+H)+.

Workup

  1. customReaction mixture
  2. extractionextracted with EtOAc
  3. washOrganic layer was washed with brine
  4. dry with materialdried over anh. Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-968eae5c152f4a1db6f4314a5af08448
Source dataset
uspto-grants-2008_08
Patent number
US07417063B2

Reaction notes

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