O-Phenylenediamine → N-(2-aminophenyl)-3-(benzyloxy)cyclobutanecarboxamide

HRID 1846812Notes

Reaction equation

HRID 1846812 reaction equation
CN(C(O[N:9]1N=[N:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.C1(N)C=CC=CC=1N.[CH2:42]([O:49][CH:50]1[CH2:53][CH:52]([C:54](O)=[O:55])[CH2:51]1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>CN(C=O)C.O>[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][C:54]([CH:52]1[CH2:53][CH:50]([O:49][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH2:51]1)=[O:55]

Participants

7

Reactant 4

HCID 7243O-PhenylenediamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 128151113-(Benzyloxy)cyclobutane-1-carboxylic acid

Product 1

HCID 67478928N-(2-aminophenyl)-3-(benzyloxy)cyclobutanecarboxamideYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

HBTU (2.06 g, 5.44 mmol) was added to a solution of diisopropyl ethylamine (1.03 mL, 5.93 mmol), o-phenylenediamine (0.54 g, 4.95 mmol), and 3-(benzyloxy)cyclobutanecarboxylic acid (1.02 g, 4.95 mmol) in DMF (20 mL) under argon atmosphere at 0° C. The mixture was stirred overnight with gradual warming to RT, then poured into water. The resulting suspension was filtered and the solid was air-dried to give N-(2-aminophenyl)-3-(benzyloxy)cyclobutanecarboxamide (1.17 g, 3.95 mmol, 80% yield) as an off-white solid.

Workup

  1. filtrationThe resulting suspension was filtered
  2. customthe solid was air-dried

Sources & evidence

ORD record
ord-6e9854f6dac24fc99d4bd0c1f07cf3fe
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Reaction notes

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