HCID 59424671, compound → HCID 59424564, compound

HRID 1261239Notes

Reaction equation

HRID 1261239 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:31][C:32]([NH:34][C:35](=[O:43])[CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[S:33])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([C:18]3[N:19](COCC[Si](C)(C)C)[CH:20]=[CH:21][N:22]=3)[S:17][C:10]=12>Cl.O1CCOCC1>[NH:19]1[CH:20]=[CH:21][N:22]=[C:18]1[C:16]1[S:17][C:10]2[C:11](=[N:12][CH:13]=[CH:14][C:9]=2[O:8][C:7]2[CH:6]=[CH:5][C:4]([NH:31][C:32]([NH:34][C:35](=[O:43])[CH2:36][C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)=[S:33])=[CH:3][C:2]=2[F:1])[CH:15]=1

Participants

4

Reactant 1

HCID 59424671HCID 59424671, compound

Product 1

HCID 59424564HCID 59424564, compoundYield 30.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
55 °C

Procedure

A solution of 112 (21 mg, 0.033 mmol) in 4N HCl in dioxane (3.5 mL) was allowed to stir at 55° C. for 1 h. The mixture was then cooled and solvent was removed under reduced pressure. The resultant gum was triturated with ether several times to form a solid material that was dried under high vacuum to afford the product 113 as a beige solid (5 mg, 28% yield). 1H NMR (400 MHz, DMSO-d6 pp 12.50 (1H, s), 11.84 (1H, s), 8.66 (1H, d, J=5.67 Hz), 8.39 (1H, s), 8.06 (1H, d, J=12.72 Hz), 7.68 (2H, s), 7.59-7.58 (2H, m), 7.36-7.30 (5H, m), 6.86 (1H, d, J=5.48 Hz), 3.83 (2H, s). MS (m/z) 504.1 (M+H).

Workup

  1. temperatureThe mixture was then cooled
  2. customsolvent was removed under reduced pressure
  3. customThe resultant gum was triturated with ether several times
  4. customto form a solid material that
  5. customwas dried under high vacuum

Sources & evidence

ORD record
ord-9fad3df397cd47918a9239daf620bc04
Source dataset
uspto-grants-2013_06
Patent number
US08470850B2

Reaction notes

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