Hydrochloric Acid → HCID 66966913, compound

HRID 1362109Notes

Reaction equation

HRID 1362109 reaction equation
C([O:5][C:6](=[O:25])/[CH:7]=[CH:8]/[C:9]1[CH:24]=[N:23][C:12]2[NH:13][C:14](=[O:22])[N:15]([CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[CH2:16][C:11]=2[CH:10]=1)(C)(C)C.C(O)(C(F)(F)F)=O.[ClH:33]>C(Cl)Cl>[ClH:33].[CH3:21][N:19]([CH3:20])[CH2:18][CH2:17][N:15]1[CH2:16][C:11]2[CH:10]=[C:9](/[CH:8]=[CH:7]/[C:6]([OH:25])=[O:5])[CH:24]=[N:23][C:12]=2[NH:13][C:14]1=[O:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 58692462HCID 58692462, compound

Product 1

HCID 66966913HCID 66966913, compoundYield 113.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (E)-3-[3-(2-dimethylamino-ethyl)-2-oxo-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidin-6-yl]acrylic acid tert-butyl ester (145 mg, 0.419 mmol) in CH2Cl2 (4 mL) was treated with TFA (2 mL). After stirring at room temperature for 30 min, the clear tan solution was concentrated in vacuo. The resulting oil was treated with anhydrous HCl (4.0 mL of 4 M solution in dioxane, 16 mmol) and stirred until the oil was converted to a solid. The solid was isolated by filtration, washed with Et2O and dried under vacuum over night to give the title compound (155 mg, quantitative) as a pale yellow solid: 1H NMR (300 MHz, DMSO-d6) δ 10.18 (s, 1H), 9.70 (br s, 1H), 8.36 (d, J=1.4 Hz, 1H), 7.92 (s, 1H), 7.55 (d, J=16.0 Hz, 1H), 6.48 (d, J=16.0 Hz, 1H), 4.53 (s, 2H), 4.50 (br s, 2H), 3.71 (t, J=5.6 Hz, 2H), 3.31 (t, J=5.6 Hz, 2H), 2.84 (s, 3H), 2.82 (s, 3H).

Workup

  1. concentrationthe clear tan solution was concentrated in vacuo
  2. stirringstirred until the oil
  3. customThe solid was isolated by filtration
  4. washwashed with Et2O
  5. customdried under vacuum over night

Sources & evidence

ORD record
ord-c511244ce44843b99614ad6ce6c4895e
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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