Triethylamine → HCID 86621214, compound

HRID 1673138Notes

Reaction equation

HRID 1673138 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([OH:15])=O)[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.O=S(Cl)Cl.[NH2:20][C:21]1[S:22][C:23]([CH:27]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[Cl:41])[NH:28][S@@:29]([C:31]([CH3:34])([CH3:33])[CH3:32])=[O:30])=[C:24]([CH3:26])[N:25]=1.CCN(CC)CC>CN(C=O)C.C(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:20][C:21]4[S:22][C:23]([CH:27]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=5[Cl:41])[NH:28][S@@:29]([C:31]([CH3:34])([CH3:32])[CH3:33])=[O:30])=[C:24]([CH3:26])[N:25]=4)=[O:15])[CH2:11][CH2:12]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 143496081-(1,3-Dioxaindan-5-yl)cyclopropane-1-carboxylic acidHCID 86621215(R)-N-((2-amino-4-methylthiazol-5-yl)(2-chlorophenyl)methyl)-2-methylpropane-2-sulfinamide

Product 1

HCID 86621214HCID 86621214, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
60 °C

Procedure

To 1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxylic acid (864 mg, 4.2 mmol) was slowly added SOCl2 (916 μL, 12.6 mmol) followed by DMF (3 drops). The reaction mixture was heated at 60° C. for 0.5 h. The excess SOCl2 was removed under vacuum. The acid chloride was then dissolved in anhydrous CH2Cl2 (6 mL) and was slowly added to a solution of (R)-N-((2-amino-4-methylthiazol-5-yl)(2-chlorophenyl)methyl)-2-methylpropane-2-sulfinamide (Isomer A) (1.35 g, 3.8 mmol) and Et3N (2.92 mL, 21.0 mmol) in anhydrous CH2Cl2 (18 mL). The reaction mixture was stirred at room temperature for 18 h, diluted with CH2Cl2 and washed with 1N HCl solution, saturated aqueous NaHCO3 solution and brine. The organic layer was dried over MgSO4 and concentrated to provide 1-(benzo[d][1,3]dioxol-5-yl)-N-(5-((2-chlorophenyl)((R)-1,1-dimethylethylsulfinamido)methyl)-4-methylthiazol-2-yl)cyclopropanecarboxamide (Isomer A) as an orange solid (1.54 g, 75%) that was used without further purification. HPLC ret. time 3.59 min, 10-99% CH3CN, 5 min run; ESI-MS 546.5 m/z (MH+).

Workup

  1. customThe excess SOCl2 was removed under vacuum
  2. dissolutionThe acid chloride was then dissolved in anhydrous CH2Cl2 (6 mL)
  3. washwashed with 1N HCl solution, saturated aqueous NaHCO3 solution and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-04e42e8797e0478da995d1ab5d49da3e
Source dataset
uspto-grants-2011_08
Patent number
US07999113B2

Reaction notes

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