Hydrochloric Acid → HCID 178505097, compound

HRID 1054559Notes

Reaction equation

HRID 1054559 reaction equation
Cl.[CH:2]1([NH:5][C:6]2[C:7]3[CH:14]=[CH:13][N:12]([C@H:15]4[C@@H:19]5[O:20]C(C)(C)[O:22][C@@H:18]5[C@@H:17]([CH2:25][N:26]([CH2:31][CH2:32][CH2:33][CH2:34][C:35]5[N:39](COCC[Si](C)(C)C)[C:38]6[CH:48]=[C:49]([Cl:56])[C:50]([C:52]([F:55])([F:54])[F:53])=[CH:51][C:37]=6[N:36]=5)[S:27]([CH3:30])(=[O:29])=[O:28])[CH2:16]4)[C:8]=3[N:9]=[CH:10][N:11]=2)[CH2:4][CH2:3]1>CO>[ClH:56].[Cl:56][C:49]1[C:50]([C:52]([F:55])([F:53])[F:54])=[CH:51][C:37]2[N:36]=[C:35]([CH2:34][CH2:33][CH2:32][CH2:31][N:26]([CH2:25][C@H:17]3[CH2:16][C@@H:15]([N:12]4[C:8]5[N:9]=[CH:10][N:11]=[C:6]([NH:5][CH:2]6[CH2:4][CH2:3]6)[C:7]=5[CH:14]=[CH:13]4)[C@H:19]([OH:20])[C@@H:18]3[OH:22])[S:27]([CH3:30])(=[O:28])=[O:29])[NH:39][C:38]=2[CH:48]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86705765HCID 86705765, compound

Product 1

HCID 178505097HCID 178505097, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 12M HCl(aq) in MeOH (1:1, 5 ml) was added to N-{[(3aR,4R,6R,6aS)-6-[4-(cyclopropylamino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]methyl}-N-{4-[6-chloro-5-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl]butyl}methanesulfonamide (155 mg, 0.19 mmol) and stirred at 40° C. for 4 hours. The reaction mixture was concentrated in vacuo. The residue was dissolved in EtOAc (150 ml), washed with sat. NaHCO3 (2×50 ml), dried over Na2SO4, filtered and evaporated. Purification by silica gel column chromatography, eluting with 7N NH3 in MeOH:DCM (5:95-1:9) gave the desired product as an oil.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc (150 ml)
  3. washwashed with sat. NaHCO3 (2×50 ml)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by silica gel column chromatography
  8. washeluting with 7N NH3 in MeOH:DCM (5:95-1:9)

Sources & evidence

ORD record
ord-60c8d40f42bb4e09b8b97d2807d3c3f3
Source dataset
uspto-grants-2016_07
Patent number
US09394310B2

Reaction notes

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