Dimethylformamide → HCID 11426492, compound

HRID 733137Notes

Reaction equation

HRID 733137 reaction equation
C1CN([P+](ON2[N:26]=[N:25][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH:34]1[CH:35]=[CH:36][C:37]2N(O)N=N[C:38]=2[CH:39]=1.[CH:44](N(CC)C(C)C)([CH3:46])[CH3:45].[Cl-:53].[NH4+].C[N:56]([CH:58]=[O:59])C>>[Cl:53][C:38]1[CH:37]=[CH:36][CH:35]=[CH:34][C:39]=1[C:22]1[CH:23]=[CH:24][CH:19]=[C:20]([N:25]2[CH:46]=[C:44]([C:58]([NH2:56])=[O:59])[CH:45]=[N:26]2)[CH:21]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2724699PyBOP

Product 1

HCID 11426492HCID 11426492, compoundYield 63%

Procedure

To a solution of the carboxylic acid (0.2 g, 0.6 mmol) in DMF (2.6 mL) were added PyBOP (0.522 g, 1 mmol), HOBT (0.135 g, 1 mmol), N,N-diisopropylethylamine (0.562 mL, 3.3 mmol) and ammonium chloride (0.071 g, 1.3 mmol), and the mixture was stirred at room temperature for 16 hours. The reaction mixture was partitioned between EtOAc and water, and the organic phase was washed with saturated sodium bicarbonate solution, brine, dried over sodium sulfate, filtered and concentrated to give the crude product, which was purified by flash chromatography using 30% EtOAc in hexanes to give 0.125 g of the titled product (63%).

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. washthe organic phase was washed with saturated sodium bicarbonate solution, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product, which
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-74d9dea13af64fe28d71f0da9cc0938e
Source dataset
uspto-grants-2009_09
Patent number
US07589116B2

Reaction notes

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