L-Tartaric acid → HCID 11696864, compound

HRID 495102Notes

Reaction equation

HRID 495102 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:15][C@@H:14]3[C@@H:11]([CH2:12][NH:13]3)[CH2:10]2)[CH:5]=[N:6][C:7]=1[Cl:8].[C:16]([OH:25])(=[O:24])[C@@H:17]([C@H:19]([C:21]([OH:23])=[O:22])[OH:20])[OH:18]>CO>[C:21]([C@@H:19]([C@H:17]([C:16]([OH:25])=[O:24])[OH:18])[OH:20])([OH:23])=[O:22].[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:15][C@@H:14]3[C@@H:11]([CH2:12][NH:13]3)[CH2:10]2)[CH:5]=[N:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 444305L-Tartaric acidHCID 10131048Sofinicline

Product 1

HCID 11696864HCID 11696864, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of the product of Example 5J (442 mg) in 5 mL methanol was slowly added a solution of L-tartaric acid (272 mg) in methanol (2 mL). During the addition, solids started to crystallize. Upon completion of the addition, the slurry was stirred at room temperature for 10 minutes. The resulting mixture was then filtered and air-dried on the filter. 1H NMR (D2O, 400 MHZ) δ 3.04 (dd, J=10, 6 Hz, 1H), 3.21 (dd, J=13, 5 Hz, 1H), 3.50-3.56 (m, 2H), 3.73 (m, 1H) 3.83 (d, J=11 Hz, 1H), 4.07 (d, J=13 Hz, 1H) 4.29 (m, 1H), 4.48 (s, 2H), 5.11 (m, 1H), 7.49 (d, J=3 Hz, 1H), 7.85 (d, J=3 Hz, 1H).

Workup

  1. additionDuring the addition, solids
  2. customto crystallize
  3. additionUpon completion of the addition
  4. filtrationThe resulting mixture was then filtered
  5. customair-dried on the filter

Sources & evidence

ORD record
ord-0b6ec37f050b4bdca29c9d1923352a1e
Source dataset
uspto-grants-2009_05
Patent number
US07538226B2

Reaction notes

Loading…