Trifluoroacetic acid → HCID 70896153, compound

HRID 2403701Notes

Reaction equation

HRID 2403701 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C([NH:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][C:17]([C:23]([N:25]3[CH2:30][CH2:29][C:28]4([CH2:38][C:37](=[O:39])[C:36]5[N:35]([CH:40]([CH3:42])[CH3:41])[N:34]=[CH:33][C:32]=5[CH2:31]4)[CH2:27][CH2:26]3)=[O:24])=[CH:18][CH:19]=2)[N:14]=1)(C)(C)C>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][C:17]([C:23]([N:25]3[CH2:26][CH2:27][C:28]4([CH2:38][C:37](=[O:39])[C:36]5[N:35]([CH:40]([CH3:42])[CH3:41])[N:34]=[CH:33][C:32]=5[CH2:31]4)[CH2:29][CH2:30]3)=[O:24])=[CH:18][CH:19]=2)[N:14]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70896136HCID 70896136, compound

Product 1

HCID 70896153HCID 70896153, compoundYield 93%

Conditions

Temperature
70 °C

Procedure

Trifluoroacetic acid (0.90 mL, 12 mmol) was added to 1′-(2-(tert-butylamino)quinoline-7-carbonyl)-1-isopropyl-4,6-dihydrospiro[indazole-5,4′-piperidin]-7(1H)-one (50 mg, 0.11 mmol). The reaction was heated to 70° C. for 3 hours, then cooled to room temperature and left stirring overnight. The reaction was concentrated to dryness and purification by reversed-phase HPLC gave the title compound (41 mg, 93%). +ESI (M+H) 418.2; HPLC retention time 2.11 minutes (Method A). 1H NMR (500 MHz, CD3OD, δ) 8.36 (d, J=9.27 Hz, 1 H), 7.97 (d, J=8.05 Hz, 1 H), 7.66 (s, 1 H), 7.53 (dd, J=8.17, 1.34 Hz, 1 H), 7.44 (s, 1 H), 7.12 (d, J=9.27 Hz, 1 H), 5.39 (quint, J=13.23, 6.68 Hz, 1 H), 3.91 (br. s., 1 H), 3.76 (br. s., 1 H), 3.46 (br. s., 2 H), 2.92 (s, 2 H), 2.67 (d, J=7.81 Hz, 2 H), 1.74 (br. s., 2 H), 1.59 (br. s., 2 H), 1.43 (br. s., 6 H).

Workup

  1. temperaturecooled to room temperature
  2. waitleft
  3. concentrationThe reaction was concentrated to dryness and purification by reversed-phase HPLC

Sources & evidence

ORD record
ord-082110822c6b4c76b1fbc5e3d59eeda9
Source dataset
uspto-grants-2014_08
Patent number
US08802688B2

Reaction notes

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