Hydrochloric Acid → HCID 66810929, compound

HRID 1097840Notes

Reaction equation

HRID 1097840 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([N:13]3[CH2:18][CH2:17][CH:16]([N:19]4[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[CH2:21][C:20]4=[O:28])[CH2:15][CH2:14]3)=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].C(OC([N:38]1[CH2:42][CH2:41]OS1(=O)=O)=O)(C)(C)C.C(N(CC)CC)C.Cl.O1CCOCC1>CN(C=O)C>[NH2:38][CH2:42][CH2:41][N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:10]=2)[C:6]([C:11]([N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:21][C:20]3=[O:28])[CH2:15][CH2:14]2)=[O:12])=[CH:7]1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 24758Sodium hydrideHCID 312751,4-DioxaneHCID 235840203-Boc-1,2,3-oxathiazolidine 2,2-dioxideHCID 24991356HCID 24991356, compound

Product 1

HCID 66810929HCID 66810929, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1-[1-(6-chloro-1H-indole-3-carbonyl)-piperidin-4-yl]-1,3-dihydro-indol-2-one (1 eq) in dry DMF was treated with NaH (1.1 eq) at 0° C. for 60 min. and then a solution of 2,2-dioxo-2λ6-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester (1.1 eq) and triethylamine (1.1 eq) in dry DMF was added and the mixture stirred at RT for 2 h. After concentration the mixture was treated with 4 M HCl in dioxan (5 eq) at 50° C. for 1 h, evaporated to dryness and partitioned between ethyl acetate and 1 N NaHCO3. The organic layer was washed with brine, separated, evaporated and the crude product chromatographed on silica gel (CH2Cl2-MeOH) to give the title compound.

Workup

  1. concentrationAfter concentration the mixture
  2. customevaporated to dryness
  3. custompartitioned between ethyl acetate and 1 N NaHCO3
  4. washThe organic layer was washed with brine
  5. customseparated
  6. customevaporated
  7. customthe crude product chromatographed on silica gel (CH2Cl2-MeOH)

Sources & evidence

ORD record
ord-48b495a6b230489c8b42709f43606f3a
Source dataset
uspto-grants-2012_03
Patent number
US08143281B2

Reaction notes

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