tert-butyl 1-((4-(1-(3-fluorobenzyl)-1H-indazol-5-ylamino)quinazolin-5-yl)methyl)piperidin-4-ylcarbamate → N-(1-(3-fluorobenzyl)-1H-indazol-5-yl)-5-((4-aminopiperidin-1-yl)methyl)quinazolin-4-amine

HRID 900326Notes

Reaction equation

HRID 900326 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:41]=[CH:42][CH:43]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][C:24]=4[CH2:26][N:27]4[CH2:32][CH2:31][CH:30]([NH:33]C(=O)OC(C)(C)C)[CH2:29][CH2:28]4)[N:19]=[CH:18][N:17]=3)=[CH:12][CH:13]=2)[CH:8]=[N:7]1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:41]=[CH:42][CH:43]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][C:24]=4[CH2:26][N:27]4[CH2:32][CH2:31][CH:30]([NH2:33])[CH2:29][CH2:28]4)[N:19]=[CH:18][N:17]=3)=[CH:12][CH:13]=2)[CH:8]=[N:7]1

Participants

3

Reactant 1

HCID 58711715tert-butyl 1-((4-(1-(3-fluorobenzyl)-1H-indazol-5-ylamino)quinazolin-5-yl)methyl)piperidin-4-ylcarbamate

Product 1

HCID 58711719N-(1-(3-fluorobenzyl)-1H-indazol-5-yl)-5-((4-aminopiperidin-1-yl)methyl)quinazolin-4-amineYield 88.3%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

21A (52 mg, 0.089 mmoL) was dissolved in a mixture of TFA/DCM (2 ml/2 ml) and stirred at rt for 10 min, then concentrated. The residue was purified by prep HPLC to give 21B (38 mg, 88%). It has an analytical HPLC retention time=1.93 min (Chromolith SpeedROD column 4.6×50 mm, 10-90% aqueous methanol containing 0.1% TFA over 4 minutes, 4 mL/min, monitoring at 254 nm) and a LC/MS M++H=482+.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-7a3961c07b14484392f1f68b9762696a
Source dataset
uspto-grants-2008_04
Patent number
US07358256B2

Reaction notes

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