Hydrochloric Acid → HCID 118235642, compound

HRID 626992Notes

Reaction equation

HRID 626992 reaction equation
[F:1][CH:2]([F:54])[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]([N:27]4[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]4)=[N:25][CH:26]=3)[C:18]([F:20])=[CH:19][C:14]2=[N:13][C:12]=1[CH2:40][O:41][C:42]1[CH:47]=[CH:46][CH:45]=[C:44]([N:48]2[CH2:52][CH2:51][O:50][C:49]2=[O:53])[CH:43]=1.[ClH:55]>O1CCOCC1>[ClH:55].[F:54][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:26]=[N:25][C:24]([N:27]4[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]4)=[N:23][CH:22]=3)[C:18]([F:20])=[CH:19][C:14]2=[N:13][C:12]=1[CH2:40][O:41][C:42]1[CH:43]=[C:44]([N:48]2[CH2:52][CH2:51][O:50][C:49]2=[O:53])[CH:45]=[CH:46][CH:47]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131735246HCID 131735246, compound

Product 1

HCID 118235642HCID 118235642, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of Example 257 (50 mg, 0.067 mmol) in 1,4-dioxane (5 mL) was added 4M HCl in 1,4-dioxane (5 mL, 20 mmol), and the reaction mixture was stirred for 3 h. The solvent was removed in vacuo, and the residue was freeze-dried, to afford the title compound (25 mg, 58%). δH (300 MHz, DMSO-d6) 9.23 (m, 2H), 8.68 (m, 1H), 8.63 (d, 2H, J 1.4 Hz), 7.86 (d, 1H, J 10.2 Hz), 7.29 (m, 4H), 7.19 (m, 1H), 7.12 (dd, 1H, J 7.8, 1.5 Hz), 7.08 (m, 2H), 6.77 (dd, 1H, J 8.0, 2.0 Hz), 5.25 (s, 2H), 4.56 (s, 2H), 4.43 (m, 2H), 4.02 (m, 6H), 3.19 (m, 4H). LCMS (ES+) 647 (M+H)+, RT 1.90 minutes.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was freeze-dried

Sources & evidence

ORD record
ord-867e4dfeabbf4884a8100f06daacfdb0
Source dataset
uspto-grants-2016_04
Patent number
US09309243B2

Reaction notes

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