Toluene → HCID 86592549, compound

HRID 1433029Notes

Reaction equation

[C:1](=[N:14][C:15]1[CH:16]=[C:17]([CH:30]=[CH:31][C:32]=1[C:33]#[N:34])[CH2:18][N:19]1[CH2:24][CH2:23][CH:22]([CH2:25][C:26](O)=[O:27])[CH2:21][C:20]1=[O:29])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OC(C)C)=O.C1(C)C=CC=CC=1.[Cl:56][C:57]1[CH:62]=[CH:61][C:60]([NH2:63])=[C:59]([NH2:64])[CH:58]=1>C1COCC1.C(Cl)Cl>[NH2:63][C:60]1[CH:61]=[CH:62][C:57]([Cl:56])=[CH:58][C:59]=1[NH:64][C:26](=[O:27])[CH2:25][CH:22]1[CH2:23][CH2:24][N:19]([CH2:18][C:17]2[CH:30]=[CH:31][C:32]([C:33]#[N:34])=[C:15]([N:14]=[C:1]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:16]=2)[C:20](=[O:29])[CH2:21]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a slurry of the {1-[3-(benzhydrylidene-amino)-4-cyano-benzyl]-2-oxo-piperidin-4-yl}-acetic acid (190 mg, 0.422 mmol) in THF (5 mL) and methylene chloride (3 mL) is added triethylamine (0.09 ml, 0.633 mmol). The solution is cooled to 0° C., and 1M isopropyl chloroformate in toluene (0.422 mL, 0.422 mmol) is added. The homogenous mixture is allowed to warm to room temperature, and 4-chloro-1,2-phenylene-diamine (150 mg, 1.06 mmol) is added. The reaction is stirred at room temperature overnight. The volatile solvents are removed, and the resulting residue is chromatographed (SiO2, 5% MeOH/EtOAc) to give N-(2-amino-5-chloro-phenyl)-2-{1-[3-(benzhydrylidene-amino)-4-cyano-benzyl]-2-oxo-piperidin-4-yl}-acetamide (200 mg, 82% yield). C34H30ClN5O2 MS m/z: 576, 578.

Workup

temperatureto warm to room temperature
customThe volatile solvents are removed
customthe resulting residue is chromatographed (SiO2, 5% MeOH/EtOAc)

Sources & evidence

ORD record: ord-64a75ca417e04ea78d7f4776f45909a9
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612075B2

Reaction notes

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