Potassium Carbonate → HCID 178451943, compound

HRID 2364800Notes

Reaction equation

HRID 2364800 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[CH:11]([C:20]3[CH:25]=[CH:24][C:23]([C:26]4[N:27]=[C:28]([C@@H:31]5[CH2:35][CH2:34][CH2:33][N:32]5[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[NH:29][CH:30]=4)=[CH:22][CH:21]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:43]([O:47][C:48]([N:50]1[CH2:54][CH2:53][CH2:52][C@H:51]1[C:55](O)=[O:56])=[O:49])([CH3:46])([CH3:45])[CH3:44].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.ClCCl>[C:39]([O:38][C:36]([N:32]1[CH2:33][CH2:34][CH2:35][C@H:31]1[C:28]1[NH:29][CH:30]=[C:26]([C:23]2[CH:24]=[CH:25][C:20]([CH:11]3[N:12]([C:13]4[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=4)[CH:8]([C:5]4[CH:6]=[CH:7][C:2]([NH:1][C:55]([C@@H:51]5[CH2:52][CH2:53][CH2:54][N:50]5[C:48]([O:47][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:49])=[O:56])=[CH:3][CH:4]=4)[CH2:9][CH2:10]3)=[CH:21][CH:22]=2)[N:27]=1)=[O:37])([CH3:42])([CH3:41])[CH3:40]

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178451915HCID 178451915, compound

Product 1

HCID 178451943HCID 178451943, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

Dissolved the product from Example 39G (285 mg, 0.502 mmol), (S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (162 mg, 0.753 mmol), HATU (305 mg, 0.803 mmol) and Hunig's base (0.263 mL, 1.506 mmol) in DMSO (5 mL) and stirred at room temperature for 1 h. Dichloromethane (50 mL) was added followed by extraction with water (2×50 mL), the organic extract dried, concentrated and the residue dissolved in methanol (10 mL) followed by the addition of potassium carbonate (400 mg, 2.89 mmol) and stirred the bright yellow solution at room temperature for 30 min. The solution was then filtered and the filtrate concentrated to an oil, which was dissolved in a 95/5 dichloromethane/methanol mixture (50 mL) and extracted with water (20 mL). The organic extract was dried and concentrated to give the title product (350 mg, 91%) as a light yellow solid and a 1/1 mixture of stereoisomers.

Workup

  1. extractionfollowed by extraction with water (2×50 mL)
  2. extractionthe organic extract
  3. customdried
  4. concentrationconcentrated
  5. dissolutionthe residue dissolved in methanol (10 mL)
  6. stirringstirred the bright yellow solution at room temperature for 30 min
  7. filtrationThe solution was then filtered
  8. concentrationthe filtrate concentrated to an oil, which
  9. dissolutionwas dissolved in a 95/5 dichloromethane/methanol mixture (50 mL)
  10. extractionextracted with water (20 mL)
  11. extractionThe organic extract
  12. customwas dried
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-b4802f07add94ae381126f2b9b1cb976
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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