Hydrochloric Acid → HCID 131736570, compound

HRID 1479115Notes

Reaction equation

HRID 1479115 reaction equation
Cl.O1CCOCC1.C(OC(=O)[NH:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[C:25]([N:27]1[CH2:41][C:30]2=[C:31]3[N:36]([N:37]=[C:29]2[CH2:28]1)[C:35]([CH3:38])=[C:34]([Cl:39])[C:33]([CH3:40])=[N:32]3)=[O:26])(C)(C)C>C(Cl)Cl>[ClH:39].[NH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[C:25]([N:27]1[CH2:41][C:30]2=[C:31]3[N:36]([N:37]=[C:29]2[CH2:28]1)[C:35]([CH3:38])=[C:34]([Cl:39])[C:33]([CH3:40])=[N:32]3)=[O:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 89662811HCID 89662811, compound

Product 1

HCID 131736570HCID 131736570, compoundYield 181.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 4M solution of HCl in 1,4-dioxane (1.67 mL; 6.7 mmol; 15 eq.) was added to a solution of Example 174 (225 mg; 0.45 mmol; 1 eq.) in DCM (10 mL) and the reaction mixture was stirred at room temperature for 15 minutes then concentrated in vacuo to afford the title compound (180 mg, 92%) as a yellow solid. 1H NMR (DMSO-d6) δ 7.92 (br s, 3H), 7.44 (ddd, J=8.4, 6.8, 4.3 Hz, 1H), 7.18 (dd, J=11.3, 2.4 Hz, 1H), 6.95 (td, J=8.4, 2.3 Hz, 1H), 4.85 (d, J=8.6 Hz, 2H), 4.59 (d, J=14.9 Hz, 2H), 4.32-4.26 (m, 2H), 3.15 (t, J=5.0 Hz, 2H), 2.86 (s, 1.6H), 2.82 (s, 1.4H), 2.62 (s, 1.4H), 2.56 (s, 1.6H). HPLC (max plot) 99.4%, Rt 2.69 min. UPLC/MS: (MS+) 404.3 ([M+H]+).

Workup

  1. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-2c2d0bb4bbaf423f9468b77526b8efc9
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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