HCID 86725101, compound → HCID 68328327, compound

HRID 634158Notes

Reaction equation

HRID 634158 reaction equation
[N:1]([C:4]1[S:8][C:7]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:13]=[C:12]3[C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)[N:26]=2)=[N:6][N:5]=1)=[N+]=[N-]>CO.C1COCC1.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[NH2:1][C:4]1[S:8][C:7]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:13]=[C:12]3[C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([N:31]3[CH2:32][CH2:33][O:34][CH2:35][CH2:36]3)[N:26]=2)=[N:6][N:5]=1

Participants

4

Reactant 1

HCID 86725101HCID 86725101, compound

Product 1

HCID 68328327HCID 68328327, compound

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 5-(5-azido-1,3,4-thiadiazol-2-yl)-3-(6-morpholinopyridin-2-yl)-1H-indole-1-carboxylate (224 mg, 0.444 mmol) in MeOH/THF (5 mL, 3:2) was added Lindlar catalyst (59.2 mg, 0.222 mmol). The mixture was stirred at RT under hydrogen for 15 h, then filtered through a plug of celite and washed with DCM/MeOH. The filtrated was concentrated to give the crude material. MS (ESI, pos. ion) m/z: 479 (M+1).

Workup

  1. filtrationfiltered through a plug of celite
  2. washwashed with DCM/MeOH
  3. concentrationThe filtrated was concentrated

Sources & evidence

ORD record
ord-7e376513f54e469db8680d3a33fd3361
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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