Hydrochloric Acid → HCID 86705761, compound

HRID 1054549Notes

Reaction equation

HRID 1054549 reaction equation
CC1(C)[O:6][C@@H:5]2[C@@H:7]([CH2:23][N:24]([CH3:49])[CH2:25][CH2:26][CH2:27][CH2:28][C:29]3[N:33](OCC[Si](C)(C)C)[C:32]4[CH:41]=[C:42]([C:45]([F:48])([F:47])[F:46])[CH:43]=[CH:44][C:31]=4[N:30]=3)[CH2:8][C@@H:9]([N:10]3[C:14]4[N:15]=[CH:16][N:17]=[C:18]([NH:19][CH:20]5[CH2:22][CH2:21]5)[C:13]=4[CH:12]=[CH:11]3)[C@@H:4]2[O:3]1.[ClH:51]>CO>[ClH:51].[ClH:51].[ClH:51].[CH:20]1([NH:19][C:18]2[C:13]3[CH:12]=[CH:11][N:10]([C@@H:9]4[CH2:8][C@H:7]([CH2:23][N:24]([CH3:49])[CH2:25][CH2:26][CH2:27][CH2:28][C:29]5[NH:33][C:32]6[CH:41]=[C:42]([C:45]([F:48])([F:47])[F:46])[CH:43]=[CH:44][C:31]=6[N:30]=5)[C@@H:5]([OH:6])[C@H:4]4[OH:3])[C:14]=3[N:15]=[CH:16][N:17]=2)[CH2:21][CH2:22]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67818703HCID 67818703, compound

Product 1

HCID 86705761HCID 86705761, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-[(3aS,4R,6R,6aR)-2,2-dimethyl-6-{[methyl({4-[6-(trifluoromethyl)-1-[2-(trimethylsilyl)ethoxy]-1H-1,3-benzodiazol-2-yl]butyl})amino]methyl}-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-N-cyclopropyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (103.7 mg, 0.14 mmol) in conc. HCl solution (2 ml, 21.54 mmol) and methanol (2 ml) was heated to 40° C. for 4 h. The reaction mixture was concentrated under reduced pressure, and the residue partitioned between sat. NaHCO3(aq) (10 ml) and EtOAc (10 ml). A small amount of MeOH (−1 ml) was added to aid dissolution, and the layers were separated. The aqueous layer was extracted with EtOAc (2×10 ml), the combined organics were then dried (MgSO4) and concentrated to afford 32.2 mg (40.5%) of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue partitioned between sat. NaHCO3(aq) (10 ml) and EtOAc (10 ml)
  3. additionA small amount of MeOH (−1 ml) was added to aid dissolution
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with EtOAc (2×10 ml)
  6. dry with materialthe combined organics were then dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3b15fce65b884e6a8eb889c361617071
Source dataset
uspto-grants-2016_07
Patent number
US09394310B2

Reaction notes

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