Hydrochloric Acid → HCID 118235654, compound

HRID 627002Notes

Reaction equation

HRID 627002 reaction equation
[F:1][CH:2]([F:40])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]1[N:15]2[CH:16]=[C:17]([C:21]3[CH:22]=[N:23][C:24]([C:27]4([OH:38])[CH2:30][N:29]([C:31]([O:33]C(C)(C)C)=[O:32])[CH2:28]4)=[N:25][CH:26]=3)[C:18]([F:20])=[CH:19][C:14]2=[N:13][C:12]=1[CH3:39].Cl>O1CCOCC1>[CH:31]([OH:33])=[O:32].[F:40][CH:2]([F:1])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]1[N:15]2[CH:16]=[C:17]([C:21]3[CH:22]=[N:23][C:24]([C:27]4([OH:38])[CH2:30][NH:29][CH2:28]4)=[N:25][CH:26]=3)[C:18]([F:20])=[CH:19][C:14]2=[N:13][C:12]=1[CH3:39]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131735247HCID 131735247, compound

Product 1

HCID 118235654HCID 118235654, compoundYield 12.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of Example 320 (92%, 346 mg, 0.573 mmol) in 1,4-dioxane (3 mL) was treated with 4M hydrogen chloride in 1,4-dioxane (2.8 mL). The mixture was placed in a sonic bath for 15 minutes, then stirred at room temperature for 2 h to give a suspension. The reaction mixture was concentrated under vacuum, and purified by preparative HPLC (Method A), to afford the title compound (36 mg, 12.5%) as a colourless solid. δH (500 MHz, CD3OD) 9.05 (d, J 1.4 Hz, 2H), 8.38 (d, J 7.1 Hz, 1H), 8.23 (s, 1H), 7.41 (d, J 10.8 Hz, 1H), 7.33-7.27 (m, 1H), 7.18 (d, J 8.0 Hz, 1H), 7.16-7.12 (m, 1H), 7.11 (dd, J 7.7, 1.8 Hz, 1H), 6.91 (t, J 74.0 Hz, 1H), 4.64 (d, J 11.8 Hz, 2H), 4.42 (s, 2H), 4.33 (d, J 11.8 Hz, 2H), 2.42 (s, 3H). Method D HPLC-MS: MH+ m/z 456, RT 0.98 minutes.

Workup

  1. customto give a suspension
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. custompurified by preparative HPLC (Method A)

Sources & evidence

ORD record
ord-2199ed0fe4cf4da79c9a6544b9a6abf6
Source dataset
uspto-grants-2016_04
Patent number
US09309243B2

Reaction notes

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