Hydrochloric Acid → HCID 71666062, compound

HRID 929066Notes

Reaction equation

HRID 929066 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]([Br:28])=[CH:24][C:23]=3[Cl: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]([Br:28])=[CH:24][C:23]=2[Cl: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 89705393HCID 89705393, compound

Product 1

HCID 71666062HCID 71666062, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-4-fluoro-5-((4-bromo-2-chlorophenyl)amino)benzo[d][1,2,3]thiadiazole-6-carboxamide (60 mg, 0.11 mmol) in CH2Cl2 (10 mL) was added 1.0 N HCl (aq., 1 mL, 1.0 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 (10 mL) and brine (10 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, 41 mg, 61.5% yield for two steps). 1H NMR (400 MHz, CD3OD): δ 11.13 (s, 1H), 8.59 (s, 1H), 7.66 (d, 1H), 7.34 (dd, 1H), 6.76 (m, 1H), 3.79 (m, 1H), 3.71 (m, 2H), 3.35 (m, 2H). MS APCI (+) m/z: m/z 492.8, [M+H].

Workup

  1. extractionThe aqueous layer was extracted by CH2Cl2 (10 mL×2)
  2. washThe combined organic layers were washed by water (10 mL) and brine (10 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-0a55eeaeef6747dd894ab778815b121e
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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