Hydrochloric Acid → HCID 24986539, compound

HRID 1640997Notes

Reaction equation

HRID 1640997 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:9]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:16]=[C:15]3[NH:40][C:41](=[O:61])[C:42]2[CH:47]=[CH:46][C:45]([C:48]([N:50]3[CH2:55][CH2:54][CH:53]([N:56]4[CH2:60][CH2:59][CH2:58][CH2:57]4)[CH2:52][CH2:51]3)=[O:49])=[CH:44][CH:43]=2)(=[O:11])=[O:10])[CH:5]=[C:6]([F:8])[CH:7]=1.Cl.CO>O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([S:9]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][N:16]=[C:15]3[NH:40][C:41](=[O:61])[C:42]2[CH:43]=[CH:44][C:45]([C:48]([N:50]3[CH2:55][CH2:54][CH:53]([N:56]4[CH2:60][CH2:59][CH2:58][CH2:57]4)[CH2:52][CH2:51]3)=[O:49])=[CH:46][CH:47]=2)(=[O:11])=[O:10])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 66736072HCID 66736072, compound

Product 1

HCID 24986539HCID 24986539, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

The crude N-[5-(3,5-difluoro-benzenesulfonyl)-1-trityl-1H-indazol-3-yl]-4-(4-pyrrolidin-1-yl-piperidine-1-carbonyl)-benzamide was treated with 15 mL of 1,4-dioxane and with 4M hydrochloric acid in 1,4-dioxane (4 mL). The mixture was stirred at room temperature for 2 days then treated with methanol (15 mL) and stirred for additional 3 hours. The solvents were removed under reduced pressure and the residue taken up with ethyl acetate, washed with 10% aqueous ammonium hydroxide, dried over sodium sulfate and evaporated to dryness. The crude was purified by flash chromatography over silica gel eluting with dichloromethane/methanol/7N NH3 in methanol 100:7:1 affording 185 mg of the title compound.

Workup

  1. stirringstirred for additional 3 hours
  2. customThe solvents were removed under reduced pressure
  3. washwashed with 10% aqueous ammonium hydroxide
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customThe crude was purified by flash chromatography over silica gel eluting with dichloromethane/methanol/7N NH3 in methanol 100:7:1 affording 185 mg of the title compound

Sources & evidence

ORD record
ord-627b2b357f1c49a1af7207ea574b2a98
Source dataset
uspto-grants-2012_02
Patent number
US08114865B2

Reaction notes

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