1,2-Dichloroethane → HCID 23571043, compound

HRID 1823900Notes

Reaction equation

[NH2:1][CH:2]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=1)[C:3]([NH:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[CH:9]2)=[O:4].[C:22]([O:26][C:27]([NH:29][CH2:30][C:31](O)=[O:32])=[O:28])([CH3:25])([CH3:24])[CH3:23].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C1COCC1>[C:22]([O:26][C:27](=[O:28])[NH:29][CH2:30][C:31](=[O:32])[NH:1][CH:2]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=1)[C:3](=[O:4])[NH:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[CH:9]2)([CH3:25])([CH3:23])[CH3:24]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-amino-2-(3-chloro-phenyl)-N-(1H-indazol-5-yl)-acetamide (0.17 mmol) and tert-butoxycarbonylamino-acetic acid (0.17 mmol) in THF (2 mL) was added HOBt (0.18 mmol). The reaction mixture was cooled to 0° C. and EDC (0.18 mmol) was added and the reaction mixture was left to stir overnight. The reaction mixture was then concentrated in vacuo and the residue was was partitioned between EtOAc and brine. The organic layer was washed with brine, dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with EtOAc:hexanes (80:20) to give the title compound in 55% yield.

Workup

waitthe reaction mixture was left
concentrationThe reaction mixture was then concentrated in vacuo
customthe residue was was partitioned between EtOAc and brine
washThe organic layer was washed with brine
dry with materialdried over sodium sulphate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel chromatography
washeluting with EtOAc:hexanes (80:20)

Sources & evidence

ORD record: ord-74af96a9b2f149909a386c1388b6d22b
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07041687B2

Reaction notes

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