Benzenamine hydrochloride (1:1) → HCID 58674816, compound

HRID 2244985Notes

Reaction equation

HRID 2244985 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][N:4]=[C:3]1[C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:31])[CH:15]([CH2:27][C:28]([OH:30])=O)[NH:16][C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=[O:18])=[CH:9][CH:8]=1.Cl.[NH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[CH3:1][N:2]1[CH2:6][CH2:5][N:4]=[C:3]1[C:7]1[CH:8]=[CH:9][C:10]([NH:13][C:14](=[O:31])[CH:15]([CH2:27][C:28]([NH:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:30])[NH:16][C:17]([NH:19][C:20]2[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=2)=[O:18])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 8870Benzenamine hydrochloride (1:1)HCID 24813Phosphorus oxychlorideHCID 68692400HCID 68692400, compound

Product 1

HCID 58674816HCID 58674816, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1:1 mixture of the R and S isomers of N-[4-(1-methyl-4,5-dihydro-1H-imidazol-2-yl)phenyl]-2-carboxymethyl-2-(4-chlorophenylaminocarbonylamino)-acetamide (from EXAMPLEs 60 and 62, 45 mg, 0.10 mmol) and aniline hydrochloride (28 mg, 0.22 mmol) in pyridine (2 mL) cooled in an ice-bath, POCl3 (0.040 mL, 0.44 mmol) was added. After being stirred at room temperature overnight, the mixture was concentrated in vacuo. The residue was purified by HPLC to the titled compound as a powder (12 mg). MS 519.1 and 521.1 (M+H, Cl pattern).

Workup

  1. temperaturecooled in an ice-bath
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe residue was purified by HPLC to the titled compound as a powder (12 mg)

Sources & evidence

ORD record
ord-330f5ef6be0142a8a3720787a7ac1e2d
Source dataset
uspto-grants-2010_03
Patent number
US07678913B2

Reaction notes

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