Pyridine → HCID 58754879, compound

HRID 1711280Notes

Reaction equation

HRID 1711280 reaction equation
[K+].[C:2]([C:4]1[N:5]=[C:6]([C:17]([O-:19])=O)[N:7]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[CH:8]=1)#[N:3].N1C=CC=CC=1.O=S(Cl)Cl.[C:30]1([C:36]2[CH:41]=[C:40]([S:42]([N:45]3[CH2:50][CH2:49][O:48][CH2:47][CH2:46]3)(=[O:44])=[O:43])[CH:39]=[CH:38][C:37]=2[NH2:51])[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]=1.C(N(CC)CC)C>C(Cl)Cl>[C:30]1([C:36]2[CH:41]=[C:40]([S:42]([N:45]3[CH2:50][CH2:49][O:48][CH2:47][CH2:46]3)(=[O:44])=[O:43])[CH:39]=[CH:38][C:37]=2[NH:51][C:17]([C:6]2[N:7]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:14])([CH3:15])[CH3:16])[CH:8]=[C:4]([C:2]#[N:3])[N:5]=2)=[O:19])[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]=1

Participants

7

Reactant 5

HCID 1049PyridineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 58754823HCID 58754823, compoundHCID 67188357potassium 4-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxylate

Product 1

HCID 58754879HCID 58754879, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A suspension of 24.0 mg (0.0785 mmol) of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylate potassium salt (as prepared in Example 11, step (d)) in CH2Cl2 (5 mL) was treated with 6.40 μL (0.0785 mmol) of pyridine for 5 min. The mixture was cooled to 0° C., and 5.70 μL (0.0785 mmol) of SOCl2 was added, allowed to warm to RT, and stirred for 30 min. A solution of 20.0 mg (0.0620 mmol) of 2-cyclohex-1-enyl-4-(morpholine-4-sulfonyl)-phenylamine (as prepared in the previous step) and triethylamine (12.0 μL, 0.0854 mmol) in CH2Cl2 (1 mL) was treated with the acid chloride solution and stirred at RT for 7 h. The mixture was diluted with CH2Cl2 (10 mL) and washed with water (1×10 mL). The organic layer was dried (MgSO4) and concentrated in vacuo to afford 15.0 mg (37%) of the title compound as a tan solid: Mass spectrum (ESI, m/z): Calcd. for C27H37N5O5SSi, 572.2 (M+H), found 572.0.

Workup

  1. temperatureto warm to RT
  2. stirringstirred at RT for 7 h
  3. washwashed with water (1×10 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-922dc7aa18ef4f25936057176593ce6a
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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