Hydrochloric Acid → HCID 118071095, compound

HRID 920814Notes

Reaction equation

HRID 920814 reaction equation
[C:1]([C:4]1[C:5]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[C:29]([Cl:34])[CH:28]=2)=[N:6][N:7]2[CH2:12][CH2:11][N:10]([C:13]([NH:15][CH:16]3[CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17]3)=[O:14])[CH2:9][C:8]=12)(=[O:3])[NH2:2].Cl.O1CCOCC1>CO>[NH:18]1[CH2:17][CH:16]([NH:15][C:13]([N:10]2[CH2:11][CH2:12][N:7]3[N:6]=[C:5]([C:27]4[CH:32]=[CH:31][C:30]([F:33])=[C:29]([Cl:34])[CH:28]=4)[C:4]([C:1]([NH2:2])=[O:3])=[C:8]3[CH2:9]2)=[O:14])[CH2:19]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 118071210HCID 118071210, compound

Product 1

HCID 118071095HCID 118071095, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of Intermediate 339A (0.25 g, 0.50 mmol) in MeOH (5 mL) was added a 4M solution of HCl in dioxane (5 mL, 20 mmol). The resulting solution was allowed to stir at RT for 4 h. The reaction mixture was then concentrated and triturated with diethyl ether to afford Intermediate 339B (0.2 g, 55%). MS(ES): m/z=393 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.84 (dd, J=7.03, 2.01 Hz, 1H) 7.64-7.70 (m, 1H), 7.45 (q, J=8.70 Hz, 1H), 7.18-7.39 (m, 2H), 6.61 (d, J=7.53 Hz, 1H), 5.53 (s, 1H), 4.73 (s, 2H), 4.13 (m, 1H), 3.97-4.04 (m, 2H), 3.83 (br. s., 2H) 3.05-3.16 (m, 4H).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-2e037cae0e80483ca31f7233d120350e
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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