HCID 86600609, compound → HCID 178490630, compound

HRID 1375729Notes

Reaction equation

HRID 1375729 reaction equation
C[Si](C)(C)CCOC[N:7]1[C:11]([CH2:12][C:13]([O:15][CH2:16][N:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:26]([F:29])([F:28])[F:27])[CH:24]=3)[C@@:19]([C:31]3[CH:36]=[C:35]([Cl:37])[CH:34]=[CH:33][C:32]=3[O:38][CH3:39])([F:30])[C:18]2=[O:40])=[O:14])=[N:10][N:9]=[N:8]1>CC#N.O>[NH:10]1[C:11]([CH2:12][C:13]([O:15][CH2:16][N:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:26]([F:27])([F:28])[F:29])[CH:24]=3)[C@@:19]([C:31]3[CH:36]=[C:35]([Cl:37])[CH:34]=[CH:33][C:32]=3[O:38][CH3:39])([F:30])[C:18]2=[O:40])=[O:14])=[N:7][N:8]=[N:9]1

Participants

4

Reactant 1

HCID 86600609HCID 86600609, compound

Product 1

HCID 178490630HCID 178490630, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

(S)-(3-(5-chloro-2-methoxyphenyl)-3-fluoro-2-oxo-6-(trifluoromethyl)indolin-1-yl)methyl 2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-tetrazol-5-yl)acetate (XIII1; n=1) (0.24 g, 0.38 mmol) was dissolved in CH3CN (20 mL), treated with aqueous HF (1 mL, 48% in H2O), and stirred at rt. until the starting material was completely consumed (as judged by HPLC). The mixture was neutralized with aqueous NaHCO3, and the CH3CN removed under reduced pressure. The aqueous layer was extracted with EtOAc, and the organic layer was then dried over MgSO4, filtered and concentrated. The isolated white solid was lyophilized to afford the title compund (0.14 g, 71% yield). 1H NMR (500 MHz, DMSO): δ 3.45 (s, 3 H), 5.79 (s, 2 H), 5.87 (d, J=10.96 Hz, 1 H), 5.91 (s, 2 H), 7.07 (d, J=8.85 Hz, 1 H), 7.47 (s, 2 H), 7.52 (dd, J=2.44, 8.85 Hz, 1 H), 7.72 (s, 2 H). LRMS: 500 (M). HRMS Calculated 498.8000 (M−H) found 498.8003.

Workup

  1. customuntil the starting material was completely consumed (as judged by HPLC)
  2. customthe CH3CN removed under reduced pressure
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialthe organic layer was then dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford the title compund (0.14 g, 71% yield)

Sources & evidence

ORD record
ord-5113497ffe2e486e9a10e0459d700293
Source dataset
uspto-grants-2007_01
Patent number
US07169803B2

Reaction notes

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