HCID 68734150, compound → HCID 68758474, compound

HRID 1798499Notes

Reaction equation

HRID 1798499 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[C:22]([C:26]4[CH:31]=[C:30]([NH:32][CH:33]5[CH2:35][CH2:34]5)[N:29]=[C:28]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=5)[CH:27]=4)[CH:23]=[N:24][CH:25]=3)=[CH:16][CH:15]=2)[CH2:9]1)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:7][C@@H:8]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]3[CH:21]=[C:22]([C:26]4[CH:31]=[C:30]([NH:32][CH:33]5[CH2:34][CH2:35]5)[N:29]=[C:28]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=5)[CH:27]=4)[CH:23]=[N:24][CH:25]=3)=[CH:18][CH:19]=2)[CH2:9]1

Participants

3

Reactant 1

HCID 68734150HCID 68734150, compound

Product 1

HCID 68758474HCID 68758474, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of {(R)-1-[4-(6′-cyclopropylamino-[2,2′;4′,3″]terpyridin-5″-yl)-benzyl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester (step 1) (1 eq, 0.204 mmol, 115 mg) in DCM/TFA (1 ml of a 3:1 mixture) is stirred at room temperature for 30 mins. The solvent is reduced in vacuo and the residue is purified by preparative HPLC (C18, 0-100% acetonitrile in water—0.1% TFA). The appropriate fractions by HPLC are combined and concentrated in vacuo. The resulting residue is dissolved in MeOH and loaded onto a SCX-2 cartridge eluting with MeOH and 2M NH3 in MeOH. The methanolic ammonia fractions are combined, concentrated in vacuo and dried under vacuum to afford the title compound; [M+H]+ 463.

Workup

  1. customthe residue is purified by preparative HPLC (C18, 0-100% acetonitrile in water—0.1% TFA)
  2. concentrationconcentrated in vacuo
  3. dissolutionThe resulting residue is dissolved in MeOH
  4. washeluting with MeOH and 2M NH3 in MeOH
  5. concentrationconcentrated in vacuo
  6. customdried under vacuum

Sources & evidence

ORD record
ord-24a442c71af74efd96b3754f710c333d
Source dataset
uspto-grants-2013_01
Patent number
US08343966B2

Reaction notes

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