Sodium Iodide → HCID 20740204, compound

HRID 1883153Notes

Reaction equation

HRID 1883153 reaction equation
[C:1]([C@@H:3]([NH:8][C:9]([C@@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]1[NH:17][C:18]([C:20]1[N:21]([CH2:29][CH2:30][CH2:31]Cl)[C:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])=[O:10])[CH2:4][CH:5]([CH3:7])[CH3:6])#[N:2].[I-].[Na+].C(#N)C.[NH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>O>[C:1]([C@@H:3]([NH:8][C:9]([C@@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]1[NH:17][C:18]([C:20]1[N:21]([CH2:29][CH2:30][CH2:31][N:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)[C:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])=[O:10])[CH2:4][CH:5]([CH3:7])[CH3:6])#[N:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 8082PiperidineHCID 60083651HCID 60083651, compound

Product 1

HCID 20740204HCID 20740204, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To 1-(3-chloro-propyl)-1H-indole-2-carboxylic acid [(1S,2R)-2-((S)-1-cyano-3-methyl-butylcarbamoyl)cyclohexyl]-amide (200 mg, 0.44 mmol) was added sodium iodide (66 mg, 0.44 mmol), acetonitrile (2 mL), and piperidine (0.1 mL, 1.3 mmol). The reaction mixture was heated to 50° C. and stirred for 24 hrs. Water (15 mL) was added to the reaction and extracted with three 20 mL portions of ethyl acetate. The combined organics were washed with saturated NaHCO3 (20 mL), dried on sodium sulfate, and concentrated. Purification by column chromatography (5:95 methanol:chloroform) gave 1-(3-piperidin-1-yl-propyl)-1H-indole-2-carboxylic acid [(1S,2R)-2-((S)-1-cyano-3-methyl-butylcarbamoyl)-cyclohexyl]-amide as a white solid (150 mg, 68%). MS: 506 (M+H).

Workup

  1. extractionextracted with three 20 mL portions of ethyl acetate
  2. washThe combined organics were washed with saturated NaHCO3 (20 mL)
  3. customdried on sodium sulfate
  4. concentrationconcentrated
  5. customPurification by column chromatography (5:95 methanol:chloroform)

Sources & evidence

ORD record
ord-d14b14feec624603949f75a9fc048cf9
Source dataset
uspto-grants-2004_07
Patent number
US06759428B2

Reaction notes

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