Hydrochloric Acid → HCID 68999176, compound

HRID 750109Notes

Reaction equation

HRID 750109 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:18]=1)=O)(C)(C)C.[ClH:30]>O1CCOCC1>[ClH:30].[O:23]([C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[O:16][CH2:15][CH2:14][C@@H:9]1[CH2:10][CH2:11][CH2:12][CH2:13][NH:8]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69000585HCID 69000585, compound

Product 1

HCID 68999176HCID 68999176, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of the product (0.250 g, 0.629 mmol) from step 1 in 4N HCl in dioxane (1.57 mL) was stirred at ambient temperature for about 1 h and then concentrated in vacuo. The residue was triturated with ether and dried in a 55° C. vacuum oven to afford the desired product as a white solid (0.187 g, 89%): 1H NMR (400 MHz, DMSO-d6): δ 8.98 (br s, 2H), 7.40 (m, 2H), 7.28 (t, 1H, J=8.4 Hz), 7.15 (tt, 1H, J1=7.6 Hz, J2=1.2 Hz), 7.02 (m, 2H), 6.73 (ddd, 1H, J1=8.4 Hz, J2=2.4 Hz, J3=0.8 Hz), 6.57 (m, 2H), 4.09 (m, 2H), 3.21 (m, 2H), 2.85 (td, 1H, J1=12 Hz, J2=2.8 Hz), 2.13 (m, 1H), 1.93 (m, 2H), 1.59 (m, 5H). MS; m/z 298 (MH+).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was triturated with ether
  3. customdried in a 55° C. vacuum oven

Sources & evidence

ORD record
ord-d53d7e378345436c903b2af2c2072f00
Source dataset
uspto-grants-2008_07
Patent number
US07402684B2

Reaction notes

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