Hydrochloric Acid → HCID 71665913, compound

HRID 929057Notes

Reaction equation

HRID 929057 reaction equation
CC1(C)[O:6][CH:5]([CH2:7][O:8][NH:9][C:10]([C:12]2[C:20]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([I:28])=[CH:24][C:23]=3[F:29])=[C:19]([F:30])[C:15]3[N:16]=[N:17][S:18][C:14]=3[CH:13]=2)=[O:11])[CH2:4][O:3]1.Cl.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[OH:6][CH:5]([CH2:4][OH:3])[CH2:7][O:8][NH:9][C:10]([C:12]1[C:20]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([I:28])=[CH:24][C:23]=2[F:29])=[C:19]([F:30])[C:15]2[N:16]=[N:17][S:18][C:14]=2[CH:13]=1)=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 89705466HCID 89705466, compound

Product 1

HCID 71665913HCID 71665913, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-4-fluoro-5-((2-fluoro-4-iodophenyl)amino)benzo[d][1,2,3]thiadiazole-6-carboxamide (229 mg, 0.41 mmol) in CH2Cl2 (10 mL) was added 1.0 N HCl (aq., 1.5 mL, 1.5 mmol). The mixture was stirred for 1 h and neutralized with saturated sodium bicarbonate (aq.). The aqueous layer was extracted by CH2Cl2 (10 mL×2). The combined organic layers were washed by water (30 mL×2) and brine (30 mL) sequentially, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica gel (CH2Cl2/MeOH, 20:1, v/v) to afford the desired product (yellow solid, 170 mg, 67.9% yield for two steps). 1H NMR (400 MHz, DMSO-d6): δ 11.98 (s, 1H), 8.40 (s, 1H), 8.20 (s, 1H), 7.58 (d, 1H), 7.33 (d, 1H), 6.64 (m, 1H), 4.86 (m, 1H), 4.62 (m, 1H), 3.87 (m, 1H), 3.72 (m, 2H), 3.33 (m, 2H, covered by the peak of water). MS APCI (+) m/z: 522.9 [M+H].

Workup

  1. extractionThe aqueous layer was extracted by CH2Cl2 (10 mL×2)
  2. washThe combined organic layers were washed by water (30 mL×2) and brine (30 mL) sequentially
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography on silica gel (CH2Cl2/MeOH, 20:1

Sources & evidence

ORD record
ord-fddb7793cfbb481da103a97f6d0f7e15
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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