Tris(hydroxymethyl)aminomethane → HCID 131725270, compound

HRID 238528Notes

Reaction equation

HRID 238528 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1.CCN(C(C)C)C(C)C.[Cl:22][C:23]1[C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=[CH:25][N:24]=1.C(O)C(N)(CO)CO>C(Cl)Cl>[Cl:22][C:23]1[C:28]([C:29]([NH:12][C:9]2[CH:10]=[CH:11][C:6]([C:2]3[NH:1][CH:5]=[CH:4][N:3]=3)=[CH:7][CH:8]=2)=[O:30])=[CH:27][CH:26]=[CH:25][N:24]=1

Participants

6

Reactant 4

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 81531DiisopropylethylamineHCID 27745412-Chloronicotinoyl chlorideHCID 235069274-(1H-Imidazol-2-yl)aniline

Product 1

HCID 131725270HCID 131725270, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A slurry of 4-imidazolylphenylamine (15.9 mg, 0.100 mmol), polymer-supported DIPEA (0.100 g, 0.362 mmol, 3.62 mmol/g loading) in CH2Cl2 (2 ml) was treated with a 2-chloropyridine-3-carbonyl chloride solution (0.10 M, 0.200 mmol, 2.0 ml, 2.0 eq) in CH2Cl2. The mixture was vortexed at RT for 14 h. Afterwards, the excess acid chloride was removed by treating the reaction mixture with polymer-supported trisamine resin (0.100 g, 0.375 mmol, 3.75 mmol/g loading). The slurry was shaken at RT for an additional 18 h. The reaction mixture was filtered, rinsed with CH2Cl2 (1 ml), and the filtrate was concentrated under reduced pressure. The resulting brown oil was used directly in the subsequent reaction.

Workup

  1. customAfterwards, the excess acid chloride was removed
  2. filtrationThe reaction mixture was filtered
  3. washrinsed with CH2Cl2 (1 ml)
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting brown oil was used directly in the subsequent reaction

Sources & evidence

ORD record
ord-4f7ce3d68d7845a9af0046d366d8f13d
Source dataset
uspto-grants-2014_02
Patent number
US08642624B2

Reaction notes

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