Hydrochloric Acid → HCID 118062498, compound

HRID 920853Notes

Reaction equation

HRID 920853 reaction equation
[C:1]([C:4]1[C:5]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[C:25]([Cl:30])[CH:24]=2)=[N:6][N:7]2[C@H:12]3[CH2:13][O:14][CH2:15][C@H:11]3[N:10](C(OC(C)(C)C)=O)[CH2:9][C:8]=12)(=[O:3])[NH2:2].Cl>O1CCOCC1>[ClH:30].[Cl:30][C:25]1[CH:24]=[C:23]([C:5]2[C:4]([C:1]([NH2:2])=[O:3])=[C:8]3[CH2:9][NH:10][C@@H:11]4[CH2:15][O:14][CH2:13][C@@H:12]4[N:7]3[N:6]=2)[CH:28]=[CH:27][C:26]=1[F:29]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118071312HCID 118071312, compound

Product 1

HCID 118062498HCID 118062498, compoundYield 198.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of Intermediate 352G (0.2 g, 0.458 mmol) in dioxane (1 mL) was added a solution of HCl in dioxane (2 mL, 8.0 mmol, 4 M). After stirring at RT for 2 h, the reaction mixture was concentrated and the crude product was triturated with hexanes to afford Intermediate 352H (0.17 g, 71%) as an off-white solid. MS(ES): −m/z=337 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.90 (ddd, J=1.8, 7.5, 14.3 Hz, 1H), 7.80-7.68 (m, 2H), 7.54-7.47 (m, 1H), 7.38 (dd, J=8.3, 9.8 Hz, 1H), 5.10 (br. s., 1H), 4.63 (br. s., 1H), 4.56 (s, 2H), 4.20-3.98 (m, 4H), 3.57 (s, 1H).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customthe crude product was triturated with hexanes

Sources & evidence

ORD record
ord-556ba41ca2b14bc8bf12b10ef5fc2138
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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