Potassium Iodide → HCID 66590184, compound

HRID 2363497Notes

Reaction equation

HRID 2363497 reaction equation
[I-].[K+].C(=O)([O-])[O-].[Na+].[Na+].[CH:9]1([CH:15]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[C:16]([NH:18][C@@H:19]2[C@H:26]3[C@H:22]([CH2:23][NH:24][CH2:25]3)[CH2:21][CH2:20]2)=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.Br[CH:34]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(C(C)=O)C>[CH:34]([N:24]1[CH2:25][C@H:26]2[C@@H:19]([NH:18][C:16](=[O:17])[CH:15]([CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]3)[CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[CH2:20][CH2:21][C@H:22]2[CH2:23]1)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 236603BromodiphenylmethaneHCID 462130532,2-Dicyclohexyl-N-((3aS,4S,6aR)-octahydrocyclopenta[c]pyrrol-4-yl)acetamide

Product 1

HCID 66590184HCID 66590184, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
90 °C

Procedure

Potassium iodide (12.48 mg, 0.075 mmol) and sodium carbonate (80 mg, 0.752 mmol) were combined with methyl ethyl ketone (5 mL) and then 2,2-dicyclohexyl-N-[(3aS,4S,6aR)-octahydrocyclopenta[c]pyrrol-4-yl]acetamide (200 mg, 0.601 mmol) from Example 53 was added followed by the addition of (bromomethylene)dibenzene (124 mg, 0.501 mmol). The reaction was heated overnight at 90° C. The reaction mixture was concentrated with a stream of nitrogen and then purified by silica gel chromatography eluting with 2-10% methanol (2 N ammonia)/dichloromethane to give the title compound: 1H NMR (500 MHz, pyridine-d5) δ ppm 7.74 (dd, J=6.7, 15.4, 1H), 7.61 (t, J=6.7, 3H), 7.35 (t, J=7.6, 4H), 7.28-7.23 (m, 3H), 4.42 (dt, J=7.4, 14.4, 1H), 4.16 (s, 1H), 2.96 (qd, J=4.2, 8.0, 1H), 2.63 (dd, J=4.1, 9.8, 1H), 2.57-2.48 (m, 1H), 2.42 (dt, J=9.4, 14.6, 2H), 2.33 (dd, J=3.7, 9.3, 1H), 2.09-1.90 (m, 3H), 1.90-1.80 (m, 3H), 1.79-1.70 (m, 4H), 1.69-1.55 (m, 6H), 1.46 (d, J=14.7, 1H), 1.39 (s, 1H), 1.33-1.00 (m, 8H), 1.00-0.89 (m, 1H); MS (ESI+) m/z 499 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated with a stream of nitrogen
  2. custompurified by silica gel chromatography
  3. washeluting with 2-10% methanol (2 N ammonia)/dichloromethane

Sources & evidence

ORD record
ord-c09f1e0250a94565b4097eaf63684888
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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