Tris(hydroxymethyl)aminomethane → HCID 131725270, compound

HRID 557382Notes

Reaction equation

HRID 557382 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-b47fee88a53843beb3e85eea42510338
Source dataset
uspto-grants-2011_11
Patent number
US08058445B2

Reaction notes

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