Trifluoroacetic acid → HCID 178504672, compound

HRID 216775Notes

Reaction equation

HRID 216775 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]([CH2:18][NH:19]C(=O)OC(C)(C)C)=[CH:16][C:15]3[C:10](=[C:11]([S:27]([CH3:30])(=[O:29])=[O:28])[CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.C(O)(C(F)(F)F)=O.Cl[C:39]1[N:47]=[CH:46][N:45]=[C:44]2[C:40]=1[NH:41][CH:42]=[N:43]2.CCN(C(C)C)C(C)C>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]([CH2:18][NH:19][C:39]3[N:47]=[CH:46][N:45]=[C:44]4[C:40]=3[N:41]=[CH:42][NH:43]4)=[CH:16][C:15]3[C:10](=[C:11]([S:27]([CH3:30])(=[O:28])=[O:29])[CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 53592776-ChloropurineHCID 57707912HCID 57707912, compound

Product 1

HCID 178504672HCID 178504672, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (2-(3-fluorophenyl)-8-(methylsulfonyl)quinolin-3-yl)methylcarbamate (18 mg, 0.042 mmol) was treated with 50% TFA in DCM (1 mL) for 30 min at rt and the reaction mixture was concentrated to dryness. The resulted solid was treated with 6-chloropurine (7.1 mg, 1.1 eq) and hunig's base (0.04 mL, 4 eq) in BunOH (1 mL) at 90° C. HPLC on reverse phase gave a white solid. 1H-NMR (400 Hz, CD3OD) δ 8.47 (s, 1H), 8.38 (dd, J=8.0, 4.0 Hz, 1H), 8.24 (s, 1H), 8.18 (dd, J=8.0, 4.0 Hz, 1H), 7.68 (t, J=8.0 Hz, 1H), 7.50-7.39 (m, 3H), 7.11 (t, J=8.0 Hz, 1H), 5.24 (s, 2H), 3.45 (s, 3H). Mass Spectrum (ESI) m/e=449 (M+1).

Workup

  1. concentrationthe reaction mixture was concentrated to dryness
  2. customHPLC on reverse phase gave a white solid

Sources & evidence

ORD record
ord-0719c31d7b6c429d8486a4d6b4ad1367
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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