Diisopropylethylamine → HCID 22046355, compound

HRID 1821740Notes

Reaction equation

HRID 1821740 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[NH:12][C:13]([NH:15][C:16]1[CH:21]=[N:20][C:19]([CH3:22])=[CH:18][N:17]=1)=[O:14])[C:6]([OH:8])=O.CN(C(ON1N=[N:38][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:47]([NH:49]C1C=CC=CN=1)C.CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[NH:12][C:13]([NH:15][C:16]1[CH:21]=[N:20][C:19]([CH3:22])=[CH:18][N:17]=1)=[O:14])[C:6]([NH:49][CH2:47][CH2:32][C:37]1[CH:36]=[CH:35][CH:34]=[CH:33][N:38]=1)=[O:8]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 118047452-(Ethylamino)pyridineHCID 220463633-Methoxy-4-[3-(5-methyl-pyrazin-2-yl)ureido]-benzoic acid

Product 1

HCID 22046355HCID 22046355, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a stirred solution of 3-methoxy-4-[3-(5-methyl-pyrazin-2-yl)ureido]-benzoic acid (30 mg, 0.1 mmol) in 1 mL NMP at RT in a capped reaction vial was added HBTU (42 mg, 0.11 mmol). The suspension was stirred for 15 minutes and then treated with 2-ethylaminopyridine (13.2 μL, 0.11 mmol) followed by Hunigs Base (35 μL, 0.2 mmol). After stirring overnight, NMP was removed by bulb to bulb transfer at 70° C. under high vacuum and the residue stirred with a mixture of CH2Cl2 (10 mL) and 10% Na2CO3 (10 mL) until complete dissolution occurred. The organics were isolated, dried (MgSO4), filtered and concentrated. The residue was triturated with EtOAc to produce a solid which was isolated by filtration (71% yield).

Workup

  1. stirringAfter stirring overnight
  2. customNMP was removed by bulb to bulb transfer at 70° C. under high vacuum
  3. stirringthe residue stirred with a mixture of CH2Cl2 (10 mL) and 10% Na2CO3 (10 mL) until complete dissolution
  4. customThe organics were isolated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was triturated with EtOAc
  9. customto produce a solid which
  10. customwas isolated by filtration (71% yield)

Sources & evidence

ORD record
ord-0538e75c51ab403484af8d40d211addf
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

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