Trifluoroacetic acid → 3-[2-(3-Aminopyrrolidine-1-carbonyl)-thiazolo[4,5-h]quinazolin-8-ylamino]-benzenesulfonamide

HRID 908352Notes

Reaction equation

HRID 908352 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][CH:15]1[CH2:19][CH2:18][N:17]([C:20]([C:22]2[S:23][C:24]3[C:33]4[N:32]=[C:31]([NH:34][C:35]5[CH:40]=[CH:39][CH:38]=[C:37]([S:41](=[O:44])(=[O:43])[NH2:42])[CH:36]=5)[N:30]=[CH:29][C:28]=4[CH:27]=[CH:26][C:25]=3[N:45]=2)=[O:21])[CH2:16]1)(C)(C)C>ClCCl>[NH2:14][CH:15]1[CH2:19][CH2:18][N:17]([C:20]([C:22]2[S:23][C:24]3[C:33]4[N:32]=[C:31]([NH:34][C:35]5[CH:36]=[C:37]([S:41]([NH2:42])(=[O:43])=[O:44])[CH:38]=[CH:39][CH:40]=5)[N:30]=[CH:29][C:28]=4[CH:27]=[CH:26][C:25]=3[N:45]=2)=[O:21])[CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59262801{1-[8-(3-Sulfamoyl-phenylamino)-thiazolo[4,5-h]quinazoline-2-carbonyl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester

Product 1

HCID 592629513-[2-(3-Aminopyrrolidine-1-carbonyl)-thiazolo[4,5-h]quinazolin-8-ylamino]-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1 ml) was added to a suspension of {1-[8-(3-Sulfamoyl-phenylamino)-thiazolo[4,5-h]quinazoline-2-carbonyl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester (87 mg, 0.15 mmol) in dichloromethane (1 ml). The reaction mixture was stirred at room temperature for 1 hour. The solution was concentrated under reduced pressure and the residue was purified by reverse phase preparative HPLC [Waters Delta-Pak C18, 15 uM, 100 A column, gradient 10%-100% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 10 minutes at 25 mL/min] to afford the title compound as a yellow solid. MS (ES+) 470, (ES−) 468. δH (d6 DMSO) 2.0-2.5 (4H, m), 3.70-4.05 (3H, m), 4.31-4.44 (2H, m), 7.37 (2H, s), 7.52 (1H, d), 7.60 (1H, t), 8.02-8.13 (6H, m), 8.69 (1H, s), 9.55 (1H, d), 10.57 (1H, s).

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customthe residue was purified by reverse phase preparative HPLC [Waters Delta-Pak C18, 15 uM, 100 A column, gradient 10%-100% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 10 minutes at 25 mL/min]

Sources & evidence

ORD record
ord-9438feb798cc47f790572155d91a844b
Source dataset
uspto-grants-2011_09
Patent number
US08017619B2

Reaction notes

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