Formaldehyde → HCID 86760255, compound

HRID 2214702Notes

Reaction equation

HRID 2214702 reaction equation
[CH2:1]=O.[NH2:3][CH2:4][CH2:5][CH:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:30]=[CH:31][C:32]=1[Cl:33])[CH2:16][N:17]([CH3:29])[C:18](=[O:28])[CH:19]=[C:20]1[C:24](=[O:25])OC(C)(C)[O:21]1>CO>[Cl:12][C:13]1[CH:14]=[C:15]([CH:30]=[CH:31][C:32]=1[Cl:33])[CH2:16][N:17]([CH3:29])[C:18]([C:19]1[CH2:1][N:3]([CH2:4][CH2:5][CH:6]2[CH2:11][CH2:10][O:9][CH2:8][CH2:7]2)[C:24](=[O:25])[C:20]=1[OH:21])=[O:28]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 27731982-(Oxan-4-yl)ethan-1-amineHCID 69655735N-(3,4-Dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-methyl-acetamide

Product 1

HCID 86760255HCID 86760255, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of paraformaldehyde (18 mg, 0.563 mmol) and 4-(2-aminoethyl)tetrahydropyran (65 mg, 0.5 mmol) in anhydrous methanol (3 mL) was warmed to 60° C. To the resulting clear homogeneous solution was added N-(3,4-dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-methyl-acetamide (172 mg, 0.5 mmol) and stirring continued for 18 h at 60° C. and an additional 6 h at room temperature. The crude reaction mixture was purified by preparative HPLC on a C18 column using water/methanol (0.1% TFA) as the eluent. The fractions containing the desired product were combined, the methanol removed under vacuum and the remaining aqueous solution extracted with ethyl acetate. The combined ethyl acetate extracts were dried over anhydrous Na2SO4, filtered and concentrated to give the title compound as a white solid (164 mg, 77% yield). 1HNMR (500 MHz, CDCl3) δ: 10.15 (1H, br s), 7.41 (1H, d, J=8.2 Hz), 7.35 (1H, s), 7.11 (1H, d, J=8.2 Hz), 4.60 (2H, s), 4.13 (2H, s), 3.93 (2H, dd, J=11, 3.7 Hz), 3.54 (2H, t, J=7.1 Hz), 3.34 (2H, t, J=11.9 Hz), 3.03 (3H, s), 1.65–1.24 (7H, m). HRMS calcd for C20H25Cl2N2O4 (M+H): 427.1191. found: 427.1179.

Workup

  1. customThe crude reaction mixture
  2. customwas purified by preparative HPLC on a C18 column
  3. additionThe fractions containing the desired product
  4. customthe methanol removed under vacuum
  5. extractionthe remaining aqueous solution extracted with ethyl acetate
  6. dry with materialThe combined ethyl acetate extracts were dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-171bf7ac339c4fb195d925b05e3db3ec
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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