Water → HCID 118308330, compound

HRID 1750581Notes

Reaction equation

Cl.[NH2:2][C@H:3]1[CH2:7][CH2:6][CH2:5][C@@H:4]1[NH:8][C:9](=[O:22])[C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=1[N:17]1[N:21]=[CH:20][CH:19]=[N:18]1.CCN(C(C)C)C(C)C.[Cl:32][C:33]1[CH:38]=[N:37][C:36](Cl)=[CH:35][N:34]=1.O>CN1C(=O)CCC1>[Cl:32][C:33]1[N:34]=[CH:35][C:36]([NH:2][C@H:3]2[CH2:7][CH2:6][CH2:5][C@@H:4]2[NH:8][C:9](=[O:22])[C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=2[N:17]2[N:18]=[CH:19][CH:20]=[N:21]2)=[N:37][CH:38]=1

Participants

Conditions

Temperature: 180 °C

Procedure

To a solution of N-[(1S,2S)-2-aminocyclopentyl]-5-methyl-2-(2H-1,2,3-triazol-2-yl)benzamide hydrochloride (Intermediate 7; 100 mg, 0.31 mmol) in NMP (1.0 ml) was added DIPEA (160 mg, 1.24 mmol) and 2,5-dichloropyrazine (CAS number 19745-07-4; 92 mg, 0.62 mmol). The resulting reaction mixture was stirred and heated under microwave irradiation at 180° C. for 15 minutes. Upon completion, the reaction mixture was poured into water (3 ml) and extracted with ethyl acetate (3×10 ml). The combined organics were dried over sodium sulfate and concentrated in vacuo. The crude product was purified by reverse phase preparative HPLC (eluted with acetonitrile/water containing 0.1% ammonia) to afford the title compound.

Workup

customThe resulting reaction mixture
extractionextracted with ethyl acetate (3×10 ml)
dry with materialThe combined organics were dried over sodium sulfate
concentrationconcentrated in vacuo
customThe crude product was purified by reverse phase preparative HPLC (eluted with acetonitrile/water containing 0.1% ammonia)

Sources & evidence

ORD record: ord-729d370e040c4b9f8556eaa0c978b1e7
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156829B2

Reaction notes

Loading…