Aniline → HCID 21914244, compound

HRID 1245558Notes

Reaction equation

HRID 1245558 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([C:13]([NH:15][NH:16][CH2:17][C:18]([O-:20])=[O:19])=[O:14])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[Na+].NC1C=CC=CC=1.CN(C([O:38]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>C(Cl)(Cl)Cl>[C:6]([NH2:7])(=[O:38])[C:5]1[CH:21]=[CH:22][CH:2]=[CH:3][CH:4]=1.[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([C:13]([NH:15][NH:16][CH2:17][C:18]([OH:20])=[O:19])=[O:14])[CH2:9][CH2:8]2)=[CH:21][CH:22]=1

Participants

7

Reactant 5

HCID 6115AnilineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 23720218HCID 23720218, compound

Product 1

HCID 21914244HCID 21914244, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Sodium N-(1-(4-chlorobenzyl)-piperazine-4-carboxamido)glycinate (20 mg, 0.060 mmol) and aniline (6.2 mg, 0.66 mmol) were dissolved in CHCl3 (1 mL). HBTU (25 mg, 0.066), HOBt (8.1 mg, 0.066 mmol) and Et3N (17 μL, 0.12 mmol) were added and the reaction mixture was stirred for 16 hr. The solvent was removed and the compound was dissolved into CH2Cl2 (2 mL). The organic layer was washed with 2N aqueous NaOH solution (2N mL), brine (1×1 mL) and concentrated. Purification via RPLC/MS afforded the desired material (6.4 mg, 21%). ESI/MS 385 (M++H, C26H24ClN3O2).

Workup

  1. customThe solvent was removed
  2. dissolutionthe compound was dissolved into CH2Cl2 (2 mL)
  3. washThe organic layer was washed with 2N aqueous NaOH solution (2N mL), brine (1×1 mL)
  4. concentrationconcentrated
  5. customPurification via RPLC/MS

Sources & evidence

ORD record
ord-aee7dd6b26ca4a82bde35f4dbc9ea0ea
Source dataset
uspto-grants-2006_10
Patent number
US07125895B1

Reaction notes

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