Formaldehyde → 1-(2-cyanoethyl)-N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N-methyl-5-oxo-2H-pyrrole-3-carboxamide

HRID 2214539Notes

Reaction equation

HRID 2214539 reaction equation
ClC1C=C(C=CC=1Cl)CN(C)C(=O)C=C1C(=O)OC(C)(C)O1.C=O.C(N(CC)CC)C.[Cl:32][C:33]1[CH:34]=[C:35]([CH:58]=[CH:59][C:60]=1[Cl:61])[CH2:36][N:37]([CH3:57])[C:38]([C:40]1[CH2:44][N:43]([CH2:45][CH2:46][C:47]([NH:49]CCC(O)=O)=O)[C:42](=[O:55])[C:41]=1[OH:56])=[O:39]>>[Cl:32][C:33]1[CH:34]=[C:35]([CH:58]=[CH:59][C:60]=1[Cl:61])[CH2:36][N:37]([CH3:57])[C:38]([C:40]1[CH2:44][N:43]([CH2:45][CH2:46][C:47]#[N:49])[C:42](=[O:55])[C:41]=1[OH:56])=[O:39]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 8471TriethylamineHCID 546917263-[3-[3-[(3,4-dichlorophenyl)methyl-methyl-carbamoyl]-4-hydroxy-5-oxo-2H-pyrrol-1-yl]propanoylamino]propanoic acidHCID 69655735N-(3,4-Dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-methyl-acetamide2×

Product 1

HCID 546982111-(2-cyanoethyl)-N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N-methyl-5-oxo-2H-pyrrole-3-carboxamideYield 45%

Procedure

N-(3,4-Dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-methyl-acetamide (Compound 37-A) was treated with paraformaldehyde and 3-aminopropionitirile with 1 equivalent of triethyl amine as described in the preparation of Compound 37. The title compound was purified by chromatography (YMC Combiprep ODS-A, 30 mm×50 mm, MeOH/H2O/0.1% TFA) to yield the title compound as a yellow foam (0.0819 g, 45% yield). 1H NMR (300 MHz, CDCl3) δ: 2.73 (t, J=6.3 Hz, 2H), 3.04 (s, 3H), 3.78 (t, J=6.3 Hz, 2H), 4.40 (s, 2H), 4.60 (s, 2H), 7.11 (dd, J=1.8 Hz, J=8.1 Hz, 1H), 7.35 (d, J=1.5 Hz, 1H), 7.43 (d, J=8.4 Hz, 1H). HRMS (M−H) calcd for C16H15N3Cl2O3: 366.04122. found: 366.0428.

Workup

  1. customThe title compound was purified by chromatography (YMC Combiprep ODS-A, 30 mm×50 mm, MeOH/H2O/0.1% TFA)

Sources & evidence

ORD record
ord-efb672fd058345e3b5d2003d996e2ad6
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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