Trifluoroacetic acid → (E)-3-(1,2,3,4,5,6-hexahydropyrido[2,3-b][1,5]diazocin-8-yl)-N-methyl-N-((3-methylbenzofuran-2-yl)methyl)acrylamide

HRID 1880017Notes

Reaction equation

HRID 1880017 reaction equation
[CH3:1][N:2]([CH2:26][C:27]1[O:28][C:29]2[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=2[C:31]=1[CH3:32])[C:3](=[O:25])/[CH:4]=[CH:5]/[C:6]1[CH:24]=[N:23][C:9]2[NH:10][CH2:11][CH2:12][CH2:13][N:14](C(OC(C)(C)C)=O)[CH2:15][C:8]=2[CH:7]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH:10]1[CH2:11][CH2:12][CH2:13][NH:14][CH2:15][C:8]2[CH:7]=[C:6](/[CH:5]=[CH:4]/[C:3]([N:2]([CH3:1])[CH2:26][C:27]3[O:28][C:29]4[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=4[C:31]=3[CH3:32])=[O:25])[CH:24]=[N:23][C:9]1=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68412763(E)-tert-butyl 8-(3-(methyl((3-methylbenzofuran-2-yl)methyl)amino)-3-oxoprop-1-enyl)-1,2,3,4-tetrahydropyrido[2,3-b][1,5]diazocine-5(6H)-carboxylate

Product 1

HCID 24891659(E)-3-(1,2,3,4,5,6-hexahydropyrido[2,3-b][1,5]diazocin-8-yl)-N-methyl-N-((3-methylbenzofuran-2-yl)methyl)acrylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(E)-tert-butyl 8-(3-(methyl((3-methylbenzofuran-2-yl)methyl)amino)-3-oxoprop-1-enyl)-1,2,3,4-tetrahydropyrido[2,3-b][1,5]diazocine-5(6H)-carboxylate (49 mg, 0.1 mmol) was dissolved in 5 mL of DCM followed by the addition of trifluoroacetic acid (5 mL). The solution was stirred for 1.5 h, then concentrated in vacuo, and subjected to prep HPLC purification to obtain the product as a white solid. Yield 25 mg (64%); 1H NMR (400 MHz, CDCl3) δ 10.1 (bs, 1H), 8.01 (m, 2H), 7.50-7.22 (m, 6H), 6.86 (d, J=16.0 Hz, 1H), 4.79 (s, 2H), 4.66 (s, 2H), 3.88 (s, 2H), 3.25 (s, 2H), 3.10 (s, 3H), 2.29 (bs, 5H); ESI MS m/z 391 [C23H26N4O2+H]+

Workup

  1. concentrationconcentrated in vacuo
  2. customHPLC purification

Sources & evidence

ORD record
ord-cbc1431d3b6a40a99455a378d0e8cc24
Source dataset
uspto-grants-2012_11
Patent number
US08318720B2

Reaction notes

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