Ammonium Chloride → HCID 66994832, compound

HRID 911914Notes

Reaction equation

HRID 911914 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][CH:34]=1)[O:5][C:6]1[CH:7]=[C:8]([S:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=2)[C:9]([NH:12][C:13]2[S:17][N:16]=[C:15]([CH:18]3[CH2:22][CH2:21][CH2:20][O:19]3)[N:14]=2)=[N:10][CH:11]=1.C[Li].C([Li])CCC.[NH4+].[Cl-:43]>C1COCC1>[ClH:43].[CH3:31][O:30][C:26]1[CH:25]=[C:24]([S:23][C:8]2[C:9]([NH:12][C:13]3[S:17][N:16]=[C:15]([CH:18]4[CH2:22][CH2:21][CH2:20][O:19]4)[N:14]=3)=[N:10][CH:11]=[C:6]([O:5][C:4]3[CH:32]=[CH:33][CH:34]=[CH:2][CH:3]=3)[CH:7]=2)[CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 57742918HCID 57742918, compoundHCID 178418339ButyllithiumHCID 178418348HCID 178418348, compound

Product 1

HCID 66994832HCID 66994832, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A 10 mL round-bottomed flask was charged with 5-(3-bromophenoxy)-3-(3-methoxyphenylthio)-N-(3-(tetrahydrofuran-2-yl)-1,2,4-thiadiazol-5-yl)pyridin-2-amine (41 mg, 0.074 mmol) and THF (2 mL). The reaction was cooled to −78° C. and methyllithium (0.055 mL, 0.088 mmol) was added and stirred for 5 minutes. Butyllithium (0.035 mL, 0.088 mmol) was added and stirred for 5 minutes. The reaction was then poured into saturated aqueous NH4Cl and extract with EtOAc. The organic layer was dried with sodium sulfate, filtered and concentrated. The residue was purified on silica gel (35% ethyl acetate in hexanes) to afford the title compound (36 mg, 95%) after HCl salt formation. 1H NMR (d6-DMSO) δ 11.47 (bs, 1H), 8.30 (bs, 1 h), 7.59 (bs, 1H), 7.37 (m, 2H), 7.28 (t, 1H), 7.14 (t, 1H), 7.03 (d, 2H), 6.88 (m, 3H), 4.04 (t, 1H), 3.90-3.75 (m, 3H), 3.72 (s, 3H), 3.57 (m, 1H), 2.25 (m, 2H). Mass spectrum (apci) m/z=479.2 (M+H—HCl).

Workup

  1. stirringstirred for 5 minutes
  2. extractionextract with EtOAc
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel (35% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-692cbae6973f4e9b9d351cb6ca74ed41
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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