Trifluoroacetic acid → HCID 59456911, compound

HRID 1711835Notes

Reaction equation

HRID 1711835 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-37e786197a74471a81b0430811a25a7e
Source dataset
uspto-grants-2010_09
Patent number
US07790709B2

Reaction notes

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