Trifluoroacetic acid → HCID 67538941, compound

HRID 1192291Notes

Reaction equation

HRID 1192291 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][CH:15]([CH2:40][C:41]1[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=1)[C:16](=[O:39])[N:17]1[CH2:22][CH2:21][N:20]([C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[C:30]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH:31]=3)[N:26]=[CH:25][N:24]=2)[CH2:19][CH2:18]1)(C)(C)C>C(Cl)Cl>[NH2:14][CH:15]([CH2:40][C:41]1[CH:42]=[CH:43][C:44]([Cl:47])=[CH:45][CH:46]=1)[C:16]([N:17]1[CH2:22][CH2:21][N:20]([C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[C:30]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH:31]=3)[N:26]=[CH:25][N:24]=2)[CH2:19][CH2:18]1)=[O:39]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67539676HCID 67539676, compound

Product 1

HCID 67538941HCID 67538941, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (4 mL) was added to a stirred solution of {1-(4-chlorobenzyl)-2-oxo-2-[4-(6-phenyl-quinazolin-4-yl)-piperazin-1-yl]-ethyl}-carbamic acid tert-butyl ester (30 mg) in DCM (10 mL) at room temperature. The solution was stirred at room temperature for 4 hours, quenched with aqueous NaOH (1N, 10 mL), diluted with EtOAc (100 mL) and washed with aqueous NaOH (2×50 mL.) The organic phase was dried over Na2SO4 and concentrated in vacuo to give 2-amino-3-(4-chlorophenyl)-1-[4-(6-phenyl-quinazolin-4-yl)-piperazin-1-yl]-propan-1-one as a colorless oil (23 mg.) 1H NMR (CDCl3, 400 MHz) δ 8.77 (1H, s), 8.02-8.00 (2H, m), 7.98 (1H, s), 7.64 (2H, d, J7.4 Hz), 7.53 (2H, t, J7.7 Hz), 7.44 (1H, t, J7.3 Hz), 7.30 (2H, d, J8.6 Hz), 7.17 (2H, d, J8.6 Hz), 3.98 (1H, t, J7.3 Hz), 3.87-3.60 (6H, m), 3.42-3.34 (2H, m), 2.97 (1H, dd, J7.4 and 13.3 Hz), 2.84 (1H, dd, J7.0 and 13.7 Hz.) The oil was taken up into THF (10 mL) and treated with HCl (1.0M in Et2O, 10 mL) and concentrated in vacuo to give the bis hydrochloride salt of 2-amino-3-(4-chlorophenyl)-1-[4-(6-phenyl-quinazolin-4-yl)-piperazin-1-yl]-propan-1-one as a solid (21 mg).

Workup

  1. customquenched with aqueous NaOH (1N, 10 mL)
  2. additiondiluted with EtOAc (100 mL)
  3. washwashed with aqueous NaOH (2×50 mL.) The organic phase
  4. dry with materialwas dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f7ace93647164a06bb7b20ace3ee359e
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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