Hydrochloric Acid → HCID 135885143, compound

HRID 2110600Notes

Reaction equation

HRID 2110600 reaction equation
[CH3:1][C:2]([CH3:39])([CH3:38])[CH2:3][CH2:4][C:5]1([NH:34]C(=O)C)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7]([C:16]2[NH:21][C:20]3[CH:22]=[CH:23][C:24]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])=[CH:25][C:19]=3[S:18](=[O:32])(=[O:31])[N:17]=2)[C:6]1=[O:33].Cl>O1CCOCC1>[NH2:34][C:5]1([CH2:4][CH2:3][C:2]([CH3:39])([CH3:38])[CH3:1])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7]([C:16]2[NH:21][C:20]3[CH:22]=[CH:23][C:24]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])=[CH:25][C:19]=3[S:18](=[O:32])(=[O:31])[N:17]=2)[C:6]1=[O:33]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 135885187HCID 135885187, compound

Product 1

HCID 135885143HCID 135885143, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of the product from Example 65 (62 mg, 0.11 mmol) in 1,4-dioxane (1 mL) was added 4N HCl (aq., 2 mL), and the resulting mixture was heated at 100° C. for 2 days. The cooled mixture was concentrated in vacuo, and was suspended in H2O to precipitate unreacted starting material. The filtrate was concentrated in vacuo to give the title compound as an off-white solid (27 mg, 44%). 1H NMR (300 MHz, DMSO-d6) δ ppm 14.44 (br s, 1H), 9.95 (s, 1H), 8.62 (br s, 2H), 8.13 (d, J=7.7 Hz, 1H), 7.59-7.74 (m, 2H), 7.48-7.59 (m, 2H), 7.42-7.48 (m, 1H), 7.33-7.39 (m, 1H), 3.01 (s, 3H), 1.94-2.12 (m, 1H), 1.76-1.94 (m, 1H), 1.01-1.18 (m, 1H), 0.70-0.80 (m, 1H), 0.69 (s, 9H).

Workup

  1. concentrationThe cooled mixture was concentrated in vacuo
  2. customto precipitate unreacted
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-53c489f5569142e6bb911b7a19c424af
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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