Sodium Iodide → HCID 57420754, compound

HRID 1713173Notes

Reaction equation

HRID 1713173 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][C:11]2[S:14][C:15]([C:17]3[CH:18]=[N:19][CH:20]=[N:21][CH:22]=3)=[CH:16][C:10]=2[CH2:9]1)=O)(C)(C)C.Cl.[O:24]1[CH2:29]COCC1.Cl[CH:31]1[CH2:36][N:35]([CH:37]2[CH2:40][CH2:39][CH2:38]2)[CH2:34][CH2:33][NH:32]1.C(N)(=O)C.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CCOC(C)=O.O.C(#N)C>[CH:37]1([N:35]2[CH2:36][CH2:31][N:32]([C:29](=[O:24])[CH2:6][N:8]3[CH2:13][CH2:12][C:11]4[S:14][C:15]([C:17]5[CH:22]=[N:21][CH:20]=[N:19][CH:18]=5)=[CH:16][C:10]=4[CH2:9]3)[CH2:33][CH2:34]2)[CH2:40][CH2:39][CH2:38]1

Participants

9

Reactant 5

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 204431481,4-Dioxane hydrochlorideHCID 59463593HCID 59463593, compoundHCID 668779022-Chloro-(4-cyclobutyl-piperazine) acetamide

Product 1

HCID 57420754HCID 57420754, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 2-pyrimidin-5-yl-6,7-dihydro-4H-thieno[3,2-c]pyridine-5-carboxylic acid tert-butyl ester (108 mg, 0.34 mmol) in EtOAc (5.0 ml) is added HCl-dioxane solution (4.0N, 2.0 ml). The resulting mixture is stirred at 50° C. overnight, and then organic solvents are evaporated. To the residue are added acetonitrile (5.0 ml), 2-chloro-(4-cyclobutyl-piperazine)-acetamide (74 mg, 0.34 mmol, 1.0 eq.), K2CO3 (94 mg, 0.68 mmol, 2.0 eq.), and NaI (30 mg). The resulting mixture is stirred at 40° C. overnight. Water (10.0 ml) is added to quench the reaction, and the acetonitrile is evaporated. The residue is extracted with DCM (10 ml×3), and the combined organic phase is dried over sodium sulfate and concentrated. The residue is purified by preparative silica gel flash chromatography (EtOAc/4% TEA) to give the title compound. 1H NMR (300 MHz, CDCl3) δ 9.08 (1H, s), 8.87 (2H, s), 7.04 (1H, s), 3.60˜3.65 (6H, m), 3.41 (2H, s), 3.09 (2H, t), 2.91 (4H, m), 2.70 (1H, m), 2.30 (4H, m), 1.66˜2.08 (6H); MS (+VE) m/z 398.2 (M++1).

Workup

  1. customorganic solvents are evaporated
  2. stirringThe resulting mixture is stirred at 40° C. overnight
  3. customto quench
  4. customthe reaction
  5. customthe acetonitrile is evaporated
  6. extractionThe residue is extracted with DCM (10 ml×3)
  7. dry with materialthe combined organic phase is dried over sodium sulfate
  8. concentrationconcentrated
  9. customThe residue is purified by preparative silica gel flash chromatography (EtOAc/4% TEA)

Sources & evidence

ORD record
ord-64576049789e4bbd98d82a0170470dc1
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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