Toluene → HCID 59174911, compound

HRID 1177646Notes

Reaction equation

HRID 1177646 reaction equation
[SH:1][C:2]1[C:7]([NH:8][C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[CH:14]3)=O)=[CH:6][CH:5]=[C:4]([C:20]2([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:22][CH2:21]2)[N:3]=1.C1(C)C=CC=CC=1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C(Cl)Cl>[NH:16]1[C:17]2[C:13](=[CH:12][C:11]([C:9]3[S:1][C:2]4[C:7]([N:8]=3)=[CH:6][CH:5]=[C:4]([C:20]3([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[CH2:22][CH2:21]3)[N:3]=4)=[CH:19][CH:18]=2)[CH:14]=[CH:15]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 178521860HCID 178521860, compound

Product 1

HCID 59174911HCID 59174911, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

To N-(2-mercapto-6-(1-phenylcyclopropyl)pyridin-3-yl)-1H-indole-5-carboxamide (360 mg, 0.934 mmol) was added toluene (9.3 mL) and camphor sulfonic acid (195 mg, 0.841 mmol) before it was heated to 100° C. for 16 h. The reaction mixture was diluted with 100 mL of DCM, added to a separatory funnel, partitioned with sodium bicarbonate (saturated, aqueous), washed 1 time with 50 mL of sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, and concentrated via rotovap to give the title compound after after flash chromatography. MS (ESI) m/z: Calculated: 367.1; Observed: 368.1 (M++H).

Workup

  1. additionadded to a separatory funnel
  2. custompartitioned with sodium bicarbonate (saturated, aqueous)
  3. washwashed 1 time with 50 mL of sodium bicarbonate (saturated, aqueous)
  4. customseparated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated via rotovap

Sources & evidence

ORD record
ord-fbd4a1d10eb8414ba1c0836d0cfbb59a
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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