1,2-Dichloroethane → HCID 57588504, compound

HRID 1782108Notes

Reaction equation

HRID 1782108 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([N:12]3[C:16]4[CH:17]=[C:18]([C:20](O)=[O:21])[NH:19][C:15]=4[N:14]=[CH:13]3)[CH:9]=[CH:10][CH:11]=2)=[CH:2]1.C(Cl)CCl.[CH3:27][NH2:28].O>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH3:27][NH:28][C:20]([C:18]1[NH:19][C:15]2[N:14]=[CH:13][N:12]([C:8]3[CH:9]=[CH:10][CH:11]=[C:6]([C:3]4[CH:4]=[CH:5][S:1][CH:2]=4)[CH:7]=3)[C:16]=2[CH:17]=1)=[O:21]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 962WaterHCID 6329MethylamineHCID 68869502HCID 68869502, compound

Product 1

HCID 57588504HCID 57588504, compoundYield 4.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(3-thien-3-ylphenyl)-1,4-dihydropyrrolo[2,3-d]imidazole-5-carboxylic acid (60 mg, 0.2 mmol), EDC (44.6 mg, 0.97 mmol) and DMAP (7.1 mg, 0.06 mmol) in dry DMF (1.5 mL) was stirred at room temperature under nitrogen for 30 minutes. Methylamine (0.5 mL, 0.97 mmol, 2M solution in THF) was then added and the mixture was allowed to stir overnight at rt. After this time, water (5 mL) was added to the mixture which was extracted with DCM (3×15 mL) and the combined organic layers washed with a saturated aqueous sodium chloride (5×10 mL), then dried over anhydrous sodium sulfate and concentrated in vacuo and the resulting crude material purified by preparative TLC (5% MeOH in CH2Cl2) to yield 2.7 mg (4.3%) of N-methyl-1-(3-thien-3-ylphenyl)-1,4-dihydropyrrolo[2,3-d]imidazole-5-carboxamide EXAMPLE 6. 1H NMR (400 MHz, CDCl3): δ=7.95 (br s, 1H), 7.73-7.71 (m, 1H), 7.57-7.42 (m, 6H), 6.59 (br s, 1H), 3.02 (d, J=5.2 Hz, 3H). MS (ES+): m/z 323.31 (100) [MH+].

Workup

  1. extractionwas extracted with DCM (3×15 mL)
  2. washthe combined organic layers washed with a saturated aqueous sodium chloride (5×10 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customthe resulting crude material purified by preparative TLC (5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-38445b03d25147f2bd695e5e6f7d387a
Source dataset
uspto-grants-2009_03
Patent number
US07498354B2

Reaction notes

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