Trifluoroacetic acid → HCID 67203172, compound

HRID 1505993Notes

Reaction equation

HRID 1505993 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[C:20]3[C:21]4[CH:36]=[CH:35][CH:34]=[N:33][C:22]=4[N:23]([S:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)(=[O:26])=[O:25])[C:19]=3[CH:18]=[N:17][C:16]=2[C:37]#[N:38])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:27]1([S:24]([N:23]2[C:19]3[CH:18]=[N:17][C:16]([C:37]#[N:38])=[C:15]([CH2:14][CH:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[C:20]=3[C:21]3[CH:36]=[CH:35][CH:34]=[N:33][C:22]2=3)(=[O:26])=[O:25])[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67201862HCID 67201862, compound

Product 1

HCID 67203172HCID 67203172, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(9-benzenesulfonyl-6-cyano-9H-dipyrido[2,3-b;4′,3′-d]pyrrol-5-ylmethyl)-piperidine-1-carboxylic acid tert-butyl ester (202 mg, 0.38 mmol) in dichloromethane (6 mL) was treated with trifluoroacetic acid (2 mL) and the resultant mixture stirred for 1 h then concentrated in vacuo. The residue was purified by flash chromatography (silica, 5 g column, SPE-NH2, 0-8% methanol in DCM) to give title compound as an off white solid (150 mg, 80%). LCMS (Method G): RT=3.07 min, M+H+=432.

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was purified by flash chromatography (silica, 5 g column, SPE-NH2, 0-8% methanol in DCM)

Sources & evidence

ORD record
ord-566f18ab9d3f4bc1bc2ae5ac5149e1b4
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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