Water → HCID 72961919, compound

HRID 1476736Notes

Reaction equation

HRID 1476736 reaction equation
C[O:2][C:3](=O)[CH:4]=[CH:5][C:6]1[CH:24]=[CH:23][C:9]2[N:10]([CH3:22])[C:11]([CH2:13][NH:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:12][C:8]=2[CH:7]=1.[OH2:26].FC(F)(F)C(O)=O.C(#[N:36])C>>[OH:26][NH:36][C:3](=[O:2])[CH:4]=[CH:5][C:6]1[CH:24]=[CH:23][C:9]2[N:10]([CH3:22])[C:11]([CH2:13][NH:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:12][C:8]=2[CH:7]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 6422Trifluoroacetic acid2×HCID 68628015HCID 68628015, compound

Product 1

HCID 72961919HCID 72961919, compound

Procedure

The titled compound (60) was prepared according to the procedures described in Step 4 of Example 1, by using 3-[2-(benzylamino-methyl)-1-methyl-1H-bezimidazol-5-yl]-acrylic acid methyl ester as the starting material HPLC: 89.6%; tR=(LC/PDA: Phenomenex Luna C18 2.0×150 mm 5μ column; 0.8 mL/min, gradient 5-65% B over 15.5 min, Solvent A: H2O with 0.1% trifluoroacetic acid; Solvent B: Acetonitrile with 0.1% trifluoroacetic acid; UV 254): 3.68 min. 1H NMR (400 MHz, DMSO-d6) δ 3.78 (3H, s), 4.37 (2H, s), 4.58 (2H, s), 6.48 (1H, d), 7.46 (3H, m), 7.55 (3H, m), 7.64 (2H, t), 7.88 (1H, s), 9.88 (1H, bs), 10.74 (1H, bs). MS (m/z): 337 [MH]+.

Workup

  1. custom3.68 min

Sources & evidence

ORD record
ord-8ecfde5f704246c39ab2d774fcf2fc8e
Source dataset
uspto-grants-2016_08
Patent number
US09402829B2

Reaction notes

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