1,2-Dichloroethane → HCID 9906800, compound

HRID 1392125Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

5,6-Diphenyl-pyrazine-2-carboxylic acid (500 mg, 1.81 mmol) from Preparation A, step (a), was dissolved in DCM (4 ml) and DMF (150 μl). DMAP (22 mg, 0.18 mmol) and 1-aminopiperidine (218 mg, 2.17 mmol) were added and the solution was cooled to 0° C. A slurry of EDC (1.99 mmol, in 2 mL DCM and 100 μl DMF) was added dropwise. The reaction mixture was stirred at 25° C. After 17 hours additional 1-aminopiperidine (40 mg, 0.40 mmol) and EDC (76 mg, 0.40 mmol) was added, and the mixture was stirred for an additional 3 hours. The crude was diluted with DCM (5 ml) and washed with a saturated solution of NaHCO3. The organic phase was dried (MgSO4), filtered and evaporated. Flash chromatography (SiO2, ethyl acetate:hexane 2:1) gave the subtitle compound (160 mg, 25%) as a white solid.

Workup

stirringthe mixture was stirred for an additional 3 hours
washwashed with a saturated solution of NaHCO3
dry with materialThe organic phase was dried (MgSO4)
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-6efd8f12d2ab419d843e8f1840c89b34
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07342019B2

Reaction notes

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