Dichloromethane → (E)-3-(4-(4-Methoxybenzyl)-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylic acid hydrochloride

HRID 83012Notes

Reaction equation

HRID 83012 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[CH:37]=[CH:36][C:13]([CH2:14][N:15]2[CH2:21][C:20]3[CH:22]=[C:23](/[CH:26]=[CH:27]/[C:28]([O:30]C(C)(C)C)=[O:29])[CH:24]=[N:25][C:19]=3[NH:18][C:17](=[O:35])[CH2:16]2)=[CH:12][CH:11]=1.[Cl:38]CCl>>[ClH:38].[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:14][N:15]2[CH2:21][C:20]3[CH:22]=[C:23](/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29])[CH:24]=[N:25][C:19]=3[NH:18][C:17](=[O:35])[CH2:16]2)=[CH:36][CH:37]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 59456913HCID 59456913, compound

Product 1

HCID 66966837(E)-3-(4-(4-Methoxybenzyl)-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylic acid hydrochloride

Procedure

Trifluoroacetic acid (1 mL) was added to a suspension of (E)-tert-butyl 3-(4(4-methoxybenzyl)-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylate (112 mg, 0.27 mmol) in dichloromethane (1 mL) at room temperature. The reaction mixture was then stirred for 1 hour and concentrated to dryness. The resulting residue was suspended in a solution of hydrochloric acid in dioxane 4N (2 mL). After 10 minutes stirring at room temperature, the precipitate was filtered and washed with diethyl ether to afford the title product as a pale yellow solid (110 mg, quantitative).

Workup

  1. concentrationconcentrated to dryness
  2. stirringAfter 10 minutes stirring at room temperature
  3. filtrationthe precipitate was filtered
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-ebac20a2f1d14fb48e4ef43467b17562
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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