HCID 86600610, compound → HCID 178490632, compound

HRID 1375730Notes

Reaction equation

HRID 1375730 reaction equation
C[Si](C)(C)CCOC[N:7]1[C:11]([CH2:12][CH2:13][C:14]([O:16][CH2:17][N:18]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([C:27]([F:30])([F:29])[F:28])[CH:25]=3)[C@@:20]([C:32]3[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:33]=3[O:39][CH3:40])([F:31])[C:19]2=[O:41])=[O:15])=[N:10][N:9]=[N:8]1>CC#N.O>[NH:10]1[C:11]([CH2:12][CH2:13][C:14]([O:16][CH2:17][N:18]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([C:27]([F:30])([F:29])[F:28])[CH:25]=3)[C@@:20]([C:32]3[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:33]=3[O:39][CH3:40])([F:31])[C:19]2=[O:41])=[O:15])=[N:7][N:8]=[N:9]1

Participants

4

Reactant 1

HCID 86600610HCID 86600610, compound

Product 1

HCID 178490632HCID 178490632, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

(S)-(3-(5-chloro-2-methoxyphenyl)-3-fluoro-2-oxo-6-(trifluoromethyl)indolin-1-yl)methyl 3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-tetrazol-5-yl)propanoate (XIII2) (0.30 g, 0.47 mmol) was dissolved in CH3CN (30 mL) and treated with aqueous HF (3 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 compound (0.21 g, 83% yield). 1H NMR (500 MHz, DMSO): δ 2.93 (t, J=7.32, Hz, 2 H), 3.14 (t, J=7.32 Hz, 2 H), 3.50 (s, 3 H), 5.89 (d, J=10.99 Hz, 1 H), 5.91 (d, J=10.99 Hz, 1 H), 7.02 (d, J=8.55 Hz, 1 H), 7.48 (s, 2 H), 7.52 (dd, J=2.44, 8.55 Hz, 2 H), 7.70 (s, 1 H), 7.72 d, J=2.44 Hz, 1 H). LRMS: 514 (M+H). HRMS Calculated 512.8270 (M−H). found 512.8266.

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

Sources & evidence

ORD record
ord-977cb2bd80324240b7da4f5d0d25b4f6
Source dataset
uspto-grants-2007_01
Patent number
US07169803B2

Reaction notes

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