HCID 178452350, compound → HCID 178513990, compound

HRID 592061Notes

Reaction equation

HRID 592061 reaction equation
[C:1]([C@H:4]1[C@H:9]2[CH2:10][C@H:6]([CH:7]=[CH:8]2)[C@H:5]1[NH:11][C:12]1[C:17]([Cl:18])=[CH:16][N:15]=[C:14]2[NH:19][C:20]([C:22]3[CH:23]=[C:24]([CH:40]=[CH:41][CH:42]=3)[C:25]([N:27]3[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]3)=[O:26])=[N:21][C:13]=12)(=[O:3])[NH2:2]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Cl:18][C:17]1[C:12]([NH:11][C@@H:5]2[C@@H:6]3[CH2:10][C@@H:9]([CH:8]=[CH:7]3)[C@@H:4]2[C:1]([NH2:2])=[O:3])=[C:13]2[N:21]=[C:20]([C:22]3[CH:42]=[CH:41][CH:40]=[C:24]([C:25]([N:27]4[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]4)=[O:26])[CH:23]=3)[NH:19][C:14]2=[N:15][CH:16]=1

Participants

4

Reactant 1

HCID 178452350HCID 178452350, compound

Product 1

HCID 178513990HCID 178513990, compoundYield 56.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

tert-butyl 4-(3-(7-((1R,2R,3S,4S)-3-carbamoylbicyclo[2.2.1]hept-5-en-2-ylamino)-6-chloro-3H-imidazo[4,5-b]pyridine-2-yl)benzoyl)piperazine-1-carboxylate (18) (160 mg, 0.27 mmol) was dissolved in 2 mL of 20% TFA solution in DCM. The reaction mixture was stirred at room temperature for 6 h. After 6 h, DCM was evaporated and the residue was triturated with ether to obtain the desired product (75 mg, 56% yield) as a light brown hygroscopic solid.

Workup

  1. waitAfter 6 h
  2. customDCM was evaporated
  3. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-99462e92bd724bd19eca9a961b9137cc
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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