Dimethylformamide → 4-[2-(4-Benzyloxy-benzoylamino)-acetyl]-piperazine-1-carboxylic acid o-tolylamide

HRID 1178064Notes

Reaction equation

HRID 1178064 reaction equation
C[CH2:2][N:3](C(C)C)[CH:4](C)C.[CH2:10]([O:17][C:18]1[CH:30]=[CH:29][C:21]([C:22]([NH:24][CH2:25][C:26]([OH:28])=O)=[O:23])=[CH:20][CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH:31]1[CH:32]=[CH:33][C:34]2N(O)N=[N:37][C:35]=2[CH:36]=1.[CH3:41]CN=C=NCCCN(C)C.Cl.[CH3:53][N:54]([CH:56]=[O:57])[CH3:55]>O>[C:34]1([CH3:41])[CH:33]=[CH:32][CH:31]=[CH:36][C:35]=1[NH:37][C:56]([N:54]1[CH2:55][CH2:4][N:3]([C:26](=[O:28])[CH2:25][NH:24][C:22](=[O:23])[C:21]2[CH:20]=[CH:19][C:18]([O:17][CH2:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)=[CH:30][CH:29]=2)[CH2:2][CH2:53]1)=[O:57]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23931762{[4-(Benzyloxy)phenyl]formamido}acetic acid

Product 1

HCID 578556454-[2-(4-Benzyloxy-benzoylamino)-acetyl]-piperazine-1-carboxylic acid o-tolylamideYield 50.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

DIPEA (136 mg, 0.182 mL, 1.05 mmol) was added to a stirred solution of (4-Benzyloxy-benzoylamino)-acetic acid (100 mg, 0.35 mmol) in DMF (1 mL). HOBT (57 mg, 0.42 mmol) and EDCI.HCl (83 mg, 0.42 mmol) were added at room temperature. After 2 minutes piperazine-1-carboxylic acid O-tolylamide TFA salt (140 mg, 0.42 mmol) was added. The reaction mixture was diluted with cold water and the resulting precipitate was filtered under reduced pressure to afford 87 mg (50.8% yield) of 4-[2-(4-benzyloxy-benzoylamino)-acetyl]-piperazine-1-carboxylic acid o-tolylamide. LCMS Purity %: 89.31, HPLC Purity %: 91.55, 1H NMR (DMSO-d6): δ 8.5-8.4 (bt, 1H), 8.2-8.1 (s, 1H), 7.9-7.8 (d, 2H), 7.4 (m, 5H), 7.2-7.0 (m, 6H) 5.2 (s, 2H), 4.2-4.1 (d, 2H), 3.5 (m, 8H), 2.2 (s, 3H).

Workup

  1. filtrationthe resulting precipitate was filtered under reduced pressure

Sources & evidence

ORD record
ord-45fb05563b4d4c21999bbc498a7e7238
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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