Trifluoroacetic acid → HCID 59456911, compound

HRID 1362055Notes

Reaction equation

HRID 1362055 reaction equation
C([O:5][C:6](=[O:22])/[CH:7]=[CH:8]/[C:9]1[CH:21]=[N:20][C:12]2[NH:13][C:14](=[O:19])[CH2:15][N:16]([CH3:18])[CH2:17][C:11]=2[CH:10]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:18][N:16]1[CH2:17][C:11]2[CH:10]=[C:9](/[CH:8]=[CH:7]/[C:6]([OH:22])=[O:5])[CH:21]=[N:20][C:12]=2[NH:13][C:14](=[O:19])[CH2:15]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59456934HCID 59456934, compound

Product 1

HCID 59456911HCID 59456911, compoundYield 163.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of (E)-3-(4-methyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylic acid tert-butyl ester (0.59 g, 1.9 mmol) in CH2Cl2 (7 mL) was treated with TFA (7 mL). After stirring at room temperature under N2 for 45 min, the clear tan solution was concentrated in vacuo. The resulting oil was treated with anhydrous HCl in dioxane (10 mL, 4.0 M) and sonicated until the oil was converted to a fine off-white solid. After stirring under N2 for 20 min, the solid was isolated by filtration, washed with Et2O, and dried under vacuum for several hours to give the title compound (0.77 g, quantitative) as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ 12.27 (bs, 1H), 11.28 (s, 1H), 8.78 (d, J=1.9 Hz, 1H), 8.32 (d, J=1.9 Hz, 1H), 7.65 (d, J=16.1 Hz, 1H), 6.63 (d, J=16.1 Hz, 1H), 4.32 (s, 2H), 3.82 (s, 2H), 2.89 (s, 3H); MS (ESI) m/e 248 (M+H)+.

Workup

  1. concentrationthe clear tan solution was concentrated in vacuo
  2. additionThe resulting oil was treated with anhydrous HCl in dioxane (10 mL, 4.0 M)
  3. customsonicated until the oil
  4. stirringAfter stirring under N2 for 20 min
  5. customthe solid was isolated by filtration
  6. washwashed with Et2O
  7. customdried under vacuum for several hours

Sources & evidence

ORD record
ord-1cf8622280da4f39a39f47e3e3845905
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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