Dichloromethane → HCID 66967079, compound

HRID 1362346Notes

Reaction equation

HRID 1362346 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-25b94303457043e99da02de00de68712
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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