1,2-Dichloroethane → N-[(7-cyanoimidazo[1,2-a]pyridine-2-yl)methyl]-N-(1,3-dioxolan-2-ylmethyl)-4-(2,4,6-trifluorobenzoyl)-1H-pyrrole-2-carboxamide

HRID 908261Notes

Reaction equation

HRID 908261 reaction equation
CN(CC1C=C(CN(C)C)C(O)=C(CN(C)C)C=1)C.[O:20]1[CH2:24][CH2:23][O:22][CH:21]1[CH2:25][NH:26][CH2:27][C:28]1[N:29]=[C:30]2[CH:35]=[C:34]([C:36]#[N:37])[CH:33]=[CH:32][N:31]2[CH:38]=1.[F:39][C:40]1[CH:55]=[C:54]([F:56])[CH:53]=[C:52]([F:57])[C:41]=1[C:42]([C:44]1[CH:45]=[C:46]([C:49](O)=[O:50])[NH:47][CH:48]=1)=[O:43].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>>[C:36]([C:34]1[CH:33]=[CH:32][N:31]2[CH:38]=[C:28]([CH2:27][N:26]([CH2:25][CH:21]3[O:20][CH2:24][CH2:23][O:22]3)[C:49]([C:46]3[NH:47][CH:48]=[C:44]([C:42](=[O:43])[C:41]4[C:40]([F:39])=[CH:55][C:54]([F:56])=[CH:53][C:52]=4[F:57])[CH:45]=3)=[O:50])[N:29]=[C:30]2[CH:35]=1)#[N:37]

Participants

7

Reactant 6

HCID 111,2-DichloroethaneHCID 70262,4,6-Tris((dimethylamino)methyl)phenolHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 534025784-(2,4,6-Trifluorobenzoyl)-1H-pyrrole-2-carboxylic acidHCID 671348252-{[(1,3-Dioxolan-2-ylmethyl)-amino]-methyl}imidazo[1,2-a]pyridine-7-carbonitrile

Product 1

HCID 58024818N-[(7-cyanoimidazo[1,2-a]pyridine-2-yl)methyl]-N-(1,3-dioxolan-2-ylmethyl)-4-(2,4,6-trifluorobenzoyl)-1H-pyrrole-2-carboxamideYield 53.4%

Procedure

To a DMF 3 mL solution of product obtained in step A (410 mg, 1.58 mmol) were added 4-(2,4,6-trifluoro-benzoyl)-1H-pyrrole-2-carboxylic acid (427 mg, 1.58 mmol), EDC (396 mg, 2.06 mmol), HOBt (316 mg, 2.06 mmol) and triethylamine (0.443 mL, 3.17 mmol). The reaction mixture was stirred overnight at room temperature. The resulting suspension was filtered and diluted with EtOAc, washed with sat. ammonium chloride aq., sat. sodium bicarbonate aq. and brine, dried over anhydrous Na2SO4, filtered and concentrated to give the title compound as foam (430 mg). LC/MS: m/z 510(M+H).

Workup

  1. filtrationThe resulting suspension was filtered
  2. additiondiluted with EtOAc
  3. washwashed with sat. ammonium chloride aq., sat. sodium bicarbonate aq. and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1231c85ee821471c97104e3856bc062e
Source dataset
uspto-grants-2011_09
Patent number
US08017605B2

Reaction notes

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