Diisopropylethylamine → HCID 178496584, compound

HRID 454339Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]2[N:11]([C@H:12]3[CH2:17][CH2:16][C@@H:15]([O:18][CH3:19])[CH2:14][CH2:13]3)[CH2:10][C:9](=[O:20])[NH:8][C:5]2=[N:6][CH:7]=1.Br[C:22]1[C:23]([NH:29][C:30](=O)CI)=[N:24][CH:25]=[C:26](Br)[N:27]=1.[CH:34](N(C(C)C)CC)([CH3:36])[CH3:35].Cl.CO[C@@H]1CC[C@H]([NH2:52])CC1>C(#N)C>[CH3:19][O:18][C@@H:15]1[CH2:16][CH2:17][C@H:12]([N:11]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([C:35]4[C:26]([CH3:25])=[N:27][C:22]([C:23]5[NH:29][CH:30]=[N:52][N:24]=5)=[CH:36][CH:34]=4)[N:3]=3)[NH:8][C:9](=[O:20])[CH2:10]2)[CH2:13][CH2:14]1

Participants

Conditions

Temperature: 55 °C

Procedure

6-Bromo-4-((cis)-4-methoxycyclohexyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one. To a solution of N-(3,5-dibromopyrazin-2-yl)-2-iodoacetamide (See Example 5.B) (1.0 g, 2.376 mmol) and diisopropylethylamine (1.038 mL, 5.94 mmol) in acetonitrile (10 mL) was added (cis)-4-methoxycyclohexanamine hydrochloride (0.413 g, 2.495 mmol). The solution was stirred at 55° C. for 3 h. The resulting precipitate was filtered and washed with acetonitrile and dried under reduced pressure to afford the title compound (0.442 g, 1.29 mmol, 55% yield). MS (ESI) m/z 341.3 [M]+, 343.3 [M+2]+.

Workup

filtrationThe resulting precipitate was filtered
washwashed with acetonitrile
customdried under reduced pressure

Sources & evidence

ORD record: ord-d2cb957335d545d592434b621fafad46
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492381B2

Reaction notes

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