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 2172068Notes

Reaction equation

HRID 2172068 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-2c7b34af31404e3998e31df12edf3e21
Source dataset
uspto-grants-2015_06
Patent number
US09051321B2

Reaction notes

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