Trifluoroacetic acid → Trifluoroacetic acid

HRID 2370625Notes

Reaction equation

HRID 2370625 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[N:24]=[C:23]3[C:18]([C:19](=[O:35])[N:20]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[Cl:34])[C:21]4[N:22]3[CH:25]=[CH:26][N:27]=4)=[CH:17][N:16]=2)=[CH:10][CH:9]=1)(C)(C)C.[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40]>C(Cl)Cl>[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[N:16]=[CH:17][C:18]3[C:19](=[O:35])[N:20]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[Cl:34])[C:21]4[N:22]([CH:25]=[CH:26][N:27]=4)[C:23]=3[N:24]=2)=[CH:10][CH:9]=1.[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68194660{4-[4-(2-Chloro-phenyl)-5-oxo-4,5-dihydro-3,4,7,9,9b-pentaaza-cyclopenta[a]naphthalen-8-ylamino]-phenyl}-carbamic acid tert-butyl ester

Product 2

HCID 6422Trifluoroacetic acidHCID 681949112-[(4-aminophenyl)amino]-6-(2-chlorophenyl)imidazo[1,2-a]pyrimido[5,4-e]pyrimidin-5(6H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of Example 56A (0.260 g, 0.516 mmol) and trifluoroacetic acid (0.397 mL, 5.16 mmol) in CH2Cl2 (5 mL) was stirred at 40° C. for 4 hours. The reaction mixture was concentrated and purified by HPLC (see protocol in Example 1F) to provide the title compound as a trifluoroacetic acid salt. The salt was treated with saturated aqueous NaHCO3 followed by filtration and drying to give a free base form of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 3.96 (s, 2H), 7.09 (d, J=1.8 Hz, 1H), 7.38-7.23 (m, 2H), 7.66-7.52 (m, 3H), 7.76-7.69 (m, 1H), 7.96-7.91 (m, 3H), 9.16 (s, 1H), 10.73-10.68 (m, 1H). MS (ESI+) m/z 404.2 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by HPLC (see protocol in Example 1F)

Sources & evidence

ORD record
ord-2bce8c3deceb475b849cf6fd16bbf52b
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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