Ether hydrochloride → HCID 11959953, compound

HRID 1508394Notes

Reaction equation

HRID 1508394 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[S:13][C:12]([CH2:21][CH2:22][CH2:23][NH:24]C(=O)OC(C)(C)C)([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=2)[N:11]([C:32]2[S:33][C:34]([CH3:37])=[N:35][N:36]=2)[N:10]=1.Cl.CCOCC>CCOCC.C(Cl)Cl>[NH2:24][CH2:23][CH2:22][CH2:21][C:12]1([C:14]2[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=2)[N:11]([C:32]2[S:33][C:34]([CH3:37])=[N:35][N:36]=2)[N:10]=[C:9]([C:3]2[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=2[F:1])[S:13]1

Participants

4

Reactant 2

HCID 10953452Ether hydrochloride2×HCID 68502983HCID 68502983, compound

Product 1

HCID 11959953HCID 11959953, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 21881112Ethyl ether methylene chlorideSolvent

Procedure

Tert-butyl 3-(5-(2,5-difluorophenyl)-2-(3-hydroxyphenyl)-3-(5-methyl-1,3,4-thiadiazol-2-yl)-2,3-dihydro-1,3,4-thiadiazol-2-yl)propylcarbamate (51 mg, 0.093 mmol) was weighed into a 25 mL flask, and dissolved in 7 mL of Et2O/DCM (1:1). HCl-Et2O (1.8 mL, 1.863 mmol) was added, and the reaction mixture was stirred at room temperature for 2 hours. An additional 20 equivalents of HCl-Et2O was added and the reaction mixture was stirred an additional 2 hours. The crude reaction mixture was concentrated in vacuo to afford a yellow solid. The solid was then purified by flash column chromatography (10-40% MeOH/DCM), affording the desired product (31 mg, 74% yield) as a yellow foam. MS ESI (+) m/z 448 (M+1) detected; 1H NMR (400 MHz, DMSO-D6) δ 7.90 (m, 1H), 7.51 (m, 2H), 7.19 (m, 1H), 6.84 (m, 2H), 6.74 (m, 1H), 3.21 (m, 1H), 2.98 (m, 1H), 2.89 (m, 2H), 2.56 (m, 3H), 2.61 (m, 1H), 2.10 (m, 1H), 1.60 (m, 1H).

Workup

  1. stirringthe reaction mixture was stirred an additional 2 hours
  2. customThe crude reaction mixture
  3. concentrationwas concentrated in vacuo
  4. customto afford a yellow solid
  5. customThe solid was then purified by flash column chromatography (10-40% MeOH/DCM)

Sources & evidence

ORD record
ord-3c71c195712c45cfa51d7ff43230eaf2
Source dataset
uspto-grants-2015_12
Patent number
US09221841B2

Reaction notes

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