Trifluoroacetic acid methylene chloride → 3-(3-Oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-acrylic acid

HRID 2097109Notes

Reaction equation

HRID 2097109 reaction equation
C([O:5][C:6](=[O:21])[CH:7]=[CH:8][C:9]1[CH:20]=[N:19][C:12]2[NH:13][CH2:14][C:15](=[O:18])[NH:16][CH2:17][C:11]=2[CH:10]=1)(C)(C)C.C(Cl)Cl.C(O)(C(F)(F)F)=O>>[O:18]=[C:15]1[CH2:14][NH:13][C:12]2[N:19]=[CH:20][C:9]([CH:8]=[CH:7][C:6]([OH:21])=[O:5])=[CH:10][C:11]=2[CH2:17][NH:16]1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 669672043-(3-Oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-acrylic acid tert-butyl ester

Product 1

HCID 669666973-(3-Oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-acrylic acidYield 61%

Procedure

3-(3-Oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-acrylic acid tert-butyl ester (96 mg, 0.31 mmol) was dissolved into 1:1 CH2Cl2/TFA (2 mL) and stirred at room temperature for 30 min. The solvents were removed in vacuo to afford the title compound as a brown solid (44 mg, 61%) and as a mixture of amide rotomers. 1H NMR (300 MHz, DMSO-d6). 8.18 (t, J=5.7 Hz, 1H), 8.07 (d, J=2.1 Hz, 1H), 7.37 (d, J=15.8 Hz, 1H), 7.35 (t, J=5.3 Hz, 1H), 6.24 (d, J=15.8 Hz, 1H), 4.28 (d, J=5.7 Hz, 2H), 3:98 (d, J=5.1 Hz, 2H), 1.45 (s, 9H).

Workup

  1. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-5c8d901de2ed4779aa67b4528113129f
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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