Imidazole → HCID 66661936, compound

HRID 2275560Notes

Reaction equation

HRID 2275560 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([N:13]3[CH2:17][CH2:16][C:15]4([C:25]5[CH:24]=[CH:23][N:22]=[CH:21][C:20]=5[C:19](=[O:26])[O:18]4)[CH2:14]3)=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.N1C=CN=C1.CN(C)C=O.C[NH:38][C@H:39]1[CH2:44][CH2:43][CH2:42][CH2:41][C@@H:40]1[NH:45][CH3:46].C(=O)([O-])[O-].[Cs+].[Cs+]>[Cu]I>[N:38]1([C:2]2[CH:7]=[CH:6][C:5]([C:8]3([C:11]([N:13]4[CH2:17][CH2:16][C@@:15]5([C:25]6[CH:24]=[CH:23][N:22]=[CH:21][C:20]=6[C:19](=[O:26])[O:18]5)[CH2:14]4)=[O:12])[CH2:10][CH2:9]3)=[CH:4][CH:3]=2)[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[N:45]=[CH:46]1

Participants

7

Reactant 5

HCID 795ImidazoleHCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 13822957(1S,2S)-(+)-N,N'-Dimethylcyclohexane-1,2-diamineHCID 66661505HCID 66661505, compound

Product 1

HCID 66661936HCID 66661936, compound

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

To a solution of 1′-{[1-(4-bromophenyl)cyclopropyl]carbonyl}-3H-spiro[furo[3,4-c]pyridine-1,3′-pyrrolidin]-3-one (30 mg, 0.00007 mol), 1H-Imidazole, 2-methyl- (7.15 mg, 0.0000871 mol) in N,N-dimethylformamide (1 mL, 0.01 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 cesium carbonate (49.7 mg, 0.000152 mol). The mixture was microwaved at 200 Celsius for 60 minutes. Then the mixture was cooled down to r.t, and filtered. The filtrate was adjusted to be acidic using TEA and stirred for 30 minutes, then diluted with methanol and purified by revised phase prep-HPLC followed by chiral HPLC to afford the desired compound, MS (ESI): 451.1 (M+H+).

Workup

  1. customThe mixture was microwaved at 200 Celsius for 60 minutes
  2. temperatureThen the mixture was cooled down
  3. filtrationfiltered
  4. additiondiluted with methanol
  5. custompurified

Sources & evidence

ORD record
ord-c95492d79f974641aa0638b45fa93508
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

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