(1S)-(+)-Camphor-10-sulphonic acid → HCID 178421850, compound

HRID 456016Notes

Reaction equation

HRID 456016 reaction equation
[CH3:1][C:2]1([CH3:34])[CH2:7][CH2:6][C:5]([C:8]2[C:13]([NH:14][C:15]([C:17]3[NH:18][CH:19]=[C:20]([C:22]#[N:23])[N:21]=3)=[O:16])=[CH:12][CH:11]=[C:10]([CH:24]3[CH2:29][C:28]([CH3:31])([CH3:30])[O:27][C:26]([CH3:33])([CH3:32])[CH2:25]3)[N:9]=2)=[CH:4][CH2:3]1.[C@:35]12([CH2:45][S:46]([OH:49])(=[O:48])=[O:47])[C:42]([CH3:44])([CH3:43])[CH:39]([CH2:40][CH2:41]1)[CH2:38][C:36]2=[O:37]>CCO>[C@:35]12([CH2:45][S:46]([OH:49])(=[O:47])=[O:48])[C:42]([CH3:44])([CH3:43])[CH:39]([CH2:40][CH2:41]1)[CH2:38][C:36]2=[O:37].[CH3:1][C:2]1([CH3:34])[CH2:7][CH2:6][C:5]([C:8]2[C:13]([NH:14][C:15]([C:17]3[NH:18][CH:19]=[C:20]([C:22]#[N:23])[N:21]=3)=[O:16])=[CH:12][CH:11]=[C:10]([CH:24]3[CH2:25][C:26]([CH3:33])([CH3:32])[O:27][C:28]([CH3:31])([CH3:30])[CH2:29]3)[N:9]=2)=[CH:4][CH2:3]1

Participants

4

Reactant 2

HCID 218580(1S)-(+)-Camphor-10-sulphonic acidHCID 178424627HCID 178424627, compound

Product 1

HCID 178421850HCID 178421850, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-cyano-1H-imidazole-2-carboxylic acid[2-(4,4-dimethyl-cyclohex-1-enyl)-6-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-pyridin-3-yl]-amide (52.4 mg, 0.113 mmol, as prepared in Example 15, step (h)) in EtOH (2 mL) was treated with (1S)-(+)-10-camphorsulfonic acid (26.4 mg, 0.113 mmol) at room temperature for 1 h. The solvents were evaporated in vacuo, and the residue was dried under high vacuum overnight. The solid was dissolved in a minimum amount of EtOH (1 mL) with sonication and heating. While warm, the solution was slowly treated with hexanes until first precipitate was seen at the surface of the solution. The mixture was allowed to stir 30 min at room temperature while material continued to precipitate. The solid was filtered and air-dried to afford the title compound (66.2 mg, 84%) as white crystals. 1H-NMR (CD3OD; 400 MHz): δ 9.17 (d, 1H, J=8.4 Hz), 8.10 (s, 1H), 7.95 (d, 1H, J=8.4 Hz), 6.39-6.32 (m, 1H), 3.76-3.64 (m, 1H), 3.38-3.34 (m, 2H), 2.80-2.75 (m, 1H), 2.75-2.65 (m, 1H), 2.54-2.45 (m, 2H), 2.40-2.30 (m, 1H), 2.25-2.18 (m, 2H), 2.10-2.00 (m, 2H), 1.98-1.86 (m, 3H), 1.76-1.66 (m, 4H), 1.65-1.56 (m, 1H), 1.47-1.38 (m, 7H), 1.30 (s, 6H), 1.15 (m, 9H), 0.87 (s, 3H). Mass spectrum (APCI, m/z): Calcd. for C27H35N5O2, 462.3 (M+H), found 462.3.

Workup

  1. customThe solvents were evaporated in vacuo
  2. customthe residue was dried under high vacuum overnight
  3. dissolutionThe solid was dissolved in a minimum amount of EtOH (1 mL) with sonication
  4. temperatureheating
  5. temperatureWhile warm
  6. additionthe solution was slowly treated with hexanes until first precipitate
  7. customto precipitate
  8. filtrationThe solid was filtered
  9. customair-dried

Sources & evidence

ORD record
ord-9e15656086354d0e91e72fa73faaa480
Source dataset
uspto-grants-2013_07
Patent number
US08497376B2

Reaction notes

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