Dimethylformamide → HCID 58449346, compound

HRID 2278730Notes

Reaction equation

HRID 2278730 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:15]([OH:17])=O)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[CH:7]=1.[CH3:18][C:19]1[N:24]=[CH:23][C:22]([CH2:25][NH2:26])=[CH:21][N:20]=1.C(N(CC)C(C)C)(C)C.CN(C)C=O>>[Br:1][C:2]1[CH:3]=[C:4]([C:15]([NH:26][CH2:25][C:22]2[CH:21]=[N:20][C:19]([CH3:18])=[N:24][CH:23]=2)=[O:17])[CH:5]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([CH3:14])=[CH:12][CH:13]=2)[CH:7]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 21294601(2-Methylpyrimidin-5-yl)methanamineHCID 58449378HCID 58449378, compound

Product 1

HCID 58449346HCID 58449346, compound

Procedure

A round bottom flask was charged with 5-bromo-4′-methylbiphenyl-3-carboxylic acid (1.00 g, 2.75 mmol), (2-methylpyrimidin-5-yl)methanamine (0.406 g, 3.30 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uroniumh (2.40 g, 6.32 mmol), N,N-diisopropylethylamine (1.91 mL, 11.0 mmol) and N,N-dimethylformamide (10 mL, 100 mmol) and the reaction stirred for 3 hours. The reaction was then quenched with water and extracted with ethyl acetate and washed with brine. The solvents were removed under reduced pressure and the residue purified by flash chromatography followed by prep HPLC to get the product as light yellow solid.

Workup

  1. customThe reaction was then quenched with water
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. customThe solvents were removed under reduced pressure
  5. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-a8cdc2ef16ba40cebdb60ec6dfb395ff
Source dataset
uspto-grants-2015_09
Patent number
US09133122B2

Reaction notes

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