Hydrochloric Acid → 2-(3-(2-Tert-butyl-7-oxo-2,4,6,7-tetrahydrospiro[indazole-5,4'-piperidine]-1'-ylcarbonyl)quinolin-6-yloxy)acetic acid

HRID 2403705Notes

Reaction equation

HRID 2403705 reaction equation
Cl.[C:2]([N:6]1[CH:40]=[C:39]2[C:8]([C:9](=[O:41])[CH2:10][C:11]3([CH2:38]2)[CH2:16][CH2:15][N:14]([C:17]([C:19]2[CH:20]=[N:21][C:22]4[C:27]([CH:28]=2)=[CH:26][C:25]([O:29][CH2:30][C:31]([O:33]C(C)(C)C)=[O:32])=[CH:24][CH:23]=4)=[O:18])[CH2:13][CH2:12]3)=[N:7]1)([CH3:5])([CH3:4])[CH3:3]>>[C:2]([N:6]1[CH:40]=[C:39]2[C:8]([C:9](=[O:41])[CH2:10][C:11]3([CH2:38]2)[CH2:16][CH2:15][N:14]([C:17]([C:19]2[CH:20]=[N:21][C:22]4[C:27]([CH:28]=2)=[CH:26][C:25]([O:29][CH2:30][C:31]([OH:33])=[O:32])=[CH:24][CH:23]=4)=[O:18])[CH2:13][CH2:12]3)=[N:7]1)([CH3:5])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 70896042Tert-butyl 2-(3-(2-tert-butyl-7-oxo-2,4,6,7-tetrahydrospiro[indazole-5,4'-piperidine]-1'-ylcarbonyl)quinolin-6-yloxy)acetate

Product 1

HCID 708961612-(3-(2-Tert-butyl-7-oxo-2,4,6,7-tetrahydrospiro[indazole-5,4'-piperidine]-1'-ylcarbonyl)quinolin-6-yloxy)acetic acidYield 100%

Procedure

Hydrochloric acid (10 mL, 40 mmol, 4 M in 1,4-dioxane) was added to tert-butyl 2-(3-(2-tert-butyl-7-oxo-2,4,6,7-tetrahydrospiro[indazole-5,4′-piperidine]-1′-ylcarbonyl)quinolin-6-yloxy)acetate (470 mg, 0.860 mmol). The reaction was stirred vigorously at room temperature for 1 hour. The reaction was concentrated. The residue was coevaporated with ethyl acetate and heptanes several times, and then dried under vacuum to provide the title compound (422 mg, 100%). +ESI (M+H) 491.4; 1H NMR (400 MHz, DMSO-d6, δ): 8.76 (d, J=2.0 Hz, 1 H), 8.35 (d, J=1.4 Hz, 1 H), 7.98 (d, J=9.2 Hz, 1 H), 7.81 (s, 1 H), 7.52 (dd, J=9.3, 2.8 Hz, 1 H), 7.42 (d, J=2.9 Hz, 1 H), 4.82 (s, 2 H), 3.57-3.73 (m, 2H), 3.34-3.50 (m, 2 H), 2.77 (s, 2 H), 2.56 (s, 2 H), 1.50 (s, 9 H), 1.44-1.58 (m, 4 H).

Workup

  1. concentrationThe reaction was concentrated
  2. customdried under vacuum

Sources & evidence

ORD record
ord-5099052158584779af69cb69a6367727
Source dataset
uspto-grants-2014_08
Patent number
US08802688B2

Reaction notes

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