HCID 58387154, compound → HCID 58387188, compound

HRID 1045097Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([N+:9]([O-])=O)=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=1>CCO.Cl.[Fe]>[Cl:1][C:2]1[C:3]([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:16][CH:17]=2)=[CH:4][C:5]([NH2:9])=[C:6]([NH2:8])[CH:7]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A 5 mL Biotage™ microwave vial was charged with Fe (285.0 mg, 5.11 mmol), a solution of compound 2-1 (166.0 mg, 0.511 mmol) in EtOH (3 mL) and diluted aqueous HCl (82 uL of 37% aqueous HCl, diluted with 0.75 mL of water). The resulting suspension was heated in a microwave synthesizer (Biotage Initiator™) at 130° C. for 10 min. The mixture was then filtered and the remaining solids were washed with EtOAc (three times, 2 mL). The filtrate and washes were combined and evaporated to dryness in vacuo. The residue was dissolved in 3:1 EtOAc/TEA and passed through a short plug of a neutral alumina. The resulting solution was evaporated to dryness in vacuo to give the crude product as brownish oil. LR-MS (API-ES): calculated for C18H15ClN2 294.1, observed m/e 295.0 (M+H)+ (Rt 3.07 min). The crude product was used in the next step without further purification.

Workup

filtrationThe mixture was then filtered
washthe remaining solids were washed with EtOAc (three times, 2 mL)
customevaporated to dryness in vacuo
dissolutionThe residue was dissolved in 3:1 EtOAc/TEA
customThe resulting solution was evaporated to dryness in vacuo

Sources & evidence

ORD record: ord-214d68db0b434eadaa056bdf44b7f903
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563746B2

Reaction notes

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