1,4-Dioxane hydrochloride → HCID 57686238, compound

HRID 1038100Notes

Reaction equation

HRID 1038100 reaction equation
Cl.O1CCOCC1.[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([NH:24][C:25]([C:27]4([N:53]([CH:55]=[O:56])[CH3:54])[CH2:31][CH2:30][N:29]([CH2:32][C:33](=[O:52])[N:34]5[CH2:39][CH:38]=[C:37]([C:40]6[CH:45]=[CH:44][C:43]([C:46]7[N:51]=[CH:50][CH:49]=[CH:48][N:47]=7)=[CH:42][CH:41]=6)[CH2:36][CH2:35]5)[CH2:28]4)=[O:26])[CH:22]=3)[N:17](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:16]=2)=[CH:11][CH:10]=1>C(Cl)Cl>[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([NH:24][C:25]([C:27]4([N:53]([CH:55]=[O:56])[CH3:54])[CH2:31][CH2:30][N:29]([CH2:32][C:33](=[O:52])[N:34]5[CH2:35][CH:36]=[C:37]([C:40]6[CH:45]=[CH:44][C:43]([C:46]7[N:47]=[CH:48][CH:49]=[CH:50][N:51]=7)=[CH:42][CH:41]=6)[CH2:38][CH2:39]5)[CH2:28]4)=[O:26])[CH:22]=3)[NH:17][N:16]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86614446HCID 86614446, compound

Product 1

HCID 57686238HCID 57686238, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Added 4M HCl/dioxane (2 ml) to a solution of 3-(Formyl-methyl-amino)-1-{2-oxo-2-[4-(4-pyrimidin-2-yl-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-ethyl}-pyrrolidine-3-carboxylic acid [3-(4-fluoro-phenyl)-1trityl-indazol-5-yl]-amide (7T) (89 mg, 0.098 mmol) in MeCl2 (2 ml) at room temperature, then stirred for 2 hours. The solvent was evaporated and the residue extracted with MeCl2 (50 ml), H2O (25 ml) and 3M NaOH (2 ml). The organic layer was separated, dried over MgSO4, filtered and solvent evaporated yielding a solid. Hexanes (2×50 ml) was added and the supernatant decanted. The residual solid was dried yielding 8T as a white solid (55 mg, 84%) LCMS (MH 659) Retention time=2.98 minutes.

Workup

  1. customThe solvent was evaporated
  2. extractionthe residue extracted with MeCl2 (50 ml), H2O (25 ml) and 3M NaOH (2 ml)
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customsolvent evaporated
  7. customyielding a solid
  8. customThe residual solid was dried

Sources & evidence

ORD record
ord-499eb72b627d4edab3412a7573cd2532
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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