Toluene → HCID 66662542, compound

HRID 557852Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]([N:14]3[CH2:18][CH2:17][C:16]4([C:26]5[CH:25]=[CH:24][N:23]=[CH:22][C:21]=5[C:20](=[O:27])[O:19]4)[CH2:15]3)=[O:13])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH:28]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2N=C1.C1(C)C=CC=CC=1.[CH3:44][N:45](C)C=O.CN[C@H]1CCCC[C@@H]1NC.C(=O)([O-])[O-].[K+].[K+]>[Cu]I>[N:28]1([C:2]2[CH:7]=[CH:6][C:5]([C:8]3([C:12]([N:14]4[CH2:18][CH2:17][C@@:16]5([C:26]6[CH:25]=[CH:24][N:23]=[CH:22][C:21]=6[C:20](=[O:27])[O:19]5)[CH2:15]4)=[O:13])[CH2:11][CH2:10][CH2:9]3)=[CH:4][CH:3]=2)[C:32]2[C:31](=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:44]=[N:45]1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 1′-{[1-(4-bromophenyl)cyclobutyl]carbonyl}-3H-spiro[furo[3,4-c]pyridine-1,3′-pyrrolidin]-3-one (30 mg, 0.00007 mol), and 1H-benzimidazole (0.010 g, 0.000087 mol) in toluene (0.5 mL, 0.005 mol) and N,N-dimethylformamide (0.5 mL, 0.006 mol), were added (1S,2S)—N,N′-dimethylcyclohexane-1,2-diamine (2.1 mg, 0.000014 mol), copper(I) iodide (1 mg, 0.000007 mol), and potassium carbonate (21.1 mg, 0.000152 mol), and the mixture was stirred at 120° C. overnight. The reaction mixture was then filtered and the filtrate was diluted with methanol. The product was purified using prep-HPLC followed by chiral HPLC. LC-MS: 465.2 (M+H)+.

Workup

filtrationThe reaction mixture was then filtered
additionthe filtrate was diluted with methanol
customThe product was purified

Sources & evidence

ORD record: ord-3a7f0c5cd8f7459a842584d1f6a08b6f
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08058288B2

Reaction notes

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