Dichloromethane → HCID 66967079, compound

HRID 2097094Notes

Reaction equation

HRID 2097094 reaction equation
C([O:5][C:6](=[O:20])/[CH:7]=[CH:8]/[C:9]1[CH:10]=[N:11][C:12]([NH2:19])=[C:13]([C:15]([OH:18])([CH3:17])[CH3:16])[CH:14]=1)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)[Cl:29]>>[ClH:29].[NH2:19][C:12]1[N:11]=[CH:10][C:9](/[CH:8]=[CH:7]/[C:6]([OH:20])=[O:5])=[CH:14][C:13]=1[C:15]([OH:18])([CH3:16])[CH3:17]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 59277621HCID 59277621, compound

Product 1

HCID 66967079HCID 66967079, compound

Procedure

A suspension of (E)-3-[6-Amino-5-(1-hydroxy-1-methyl-ethyl)-pyridin-3-yl]-acrylic acid tert-butyl ester (0.13 g, 0.47 mmol) in CH2Cl2 (6 mL) was treated with TFA (6 mL). After stirring at room temperature for 2 h, the solution was concentrated in vacuo. The resulting oil was treated with anhydrous HCl in dioxane (3 mL, 4.0 M) and sonicated until the oil was converted to a fine off-white solid. After stirring for 20 min, the suspension was concentrated. The solid was washed with Et2O, isolated by filtration and dried under vacuum. Yield: 0.11 g (92%); 1H NMR (300 MHz, DMSO-d6) δ 8.29 (d, J=1.5 Hz, 1H), 8.23 (br, s, 2H), 8.13 (d, J=1.8 Hz, 1H), 7.52 (d, J=16.1 Hz, 1H), 6.65 (d, J=16.1 Hz, 1H), 4.29 (s, 1H), 1.56 (s, 6H); ESI MS m/z 223 [C11H10N2O4+H]+

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. additionThe resulting oil was treated with anhydrous HCl in dioxane (3 mL, 4.0 M)
  3. customsonicated until the oil
  4. stirringAfter stirring for 20 min
  5. concentrationthe suspension was concentrated
  6. washThe solid was washed with Et2O
  7. customisolated by filtration
  8. customdried under vacuum

Sources & evidence

ORD record
ord-625bb1c4b31f4baf9c7df3ef531e7ee7
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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