HCID 86709943, compound → HCID 72950360, compound

HRID 1526779Notes

Reaction equation

HRID 1526779 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@@H:12]([NH:17][C:18](=[O:42])[CH2:19][NH:20][C:21](=[O:41])[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([NH:28][C:29]3[N:30](C(OC(C)(C)C)=O)[CH2:31][CH2:32][N:33]=3)[CH:23]=2)[CH2:13][C:14]([OH:16])=[O:15])[CH:5]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:7]=1>C(O)(C(F)(F)F)=O.C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([C@@H:12]([NH:17][C:18](=[O:42])[CH2:19][NH:20][C:21](=[O:41])[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([NH:28][C:29]3[NH:33][CH2:32][CH2:31][N:30]=3)[CH:23]=2)[CH2:13][C:14]([OH:16])=[O:15])[CH:5]=[C:6]([C:8]([CH3:9])([CH3:11])[CH3:10])[CH:7]=1

Participants

4

Reactant 1

HCID 86709943HCID 86709943, compound

Product 1

HCID 72950360HCID 72950360, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The crude (S)-3-(3-bromo-5-(tert-butyl)phenyl)-3-(2-(3-((1-(tert-butoxycarbonyl)-4,5-dihydro-1H-imidazol-2-yl)amino)benzamido)acetamido)propanoic acid from Step #2 was dissolved in 20% TFA in acetonitrile (10 mL) and the reaction mixture was stirred at room temperature overnight to give a colorless solution. The solvent was evaporated in vacuo to give a colorless viscous residue. The crude product was purified by reverse-phase HPLC with a gradient 10-70% CH3CN in water containing 0.05% TFA to give the desired product (Example 7), after lyophilization, as a colorless lyophilized solid (364 mg). LC/MS analysis of the product shows the desired product's mass: m/z 544 (79BrM+H), and m/z 546 (81BrM+H); Calcd for C25H30BrN5O4: 544.44. 1H NMR (400 MHz, DMSO-d6): δ 1.27 (s, 9H, (CH3)3C—), 2.71 (d, J=7.30 Hz, 2H, —CH2—COOH), 3.68 (brs, 3H), 3.92 (d, J=5.80 Hz, 2H), 5.20 (q, J=7.5 Hz, 1H, —NH—CH—CH2—COOH), 7.36 (brd, J=9.8 Hz, 2H), 7.41 (brd/m, 2H), 7.55 (t, J=7.8 Hz, 1H), 7.73 (brs, 1H), 7.79 (d, J=7.8 Hz, 1H), 8.46 (s, 2H), 1H), 8.55 (d, J=7.30 Hz, 1H), 8.80 (appt, J=5.80 Hz, 1H), 10.62 (s, 1H), 12.37 (brs, 1H, —COOH). 1H NMR spectrum of the sample was consistent with the suggested structure of the product.

Workup

  1. customto give a colorless solution
  2. customThe solvent was evaporated in vacuo
  3. customto give a colorless viscous residue
  4. customThe crude product was purified by reverse-phase HPLC with a gradient 10-70% CH3CN in water containing 0.05% TFA

Sources & evidence

ORD record
ord-e510cb887f0b48f4a63a0bfe5463d833
Source dataset
uspto-grants-2015_07
Patent number
US09085606B2

Reaction notes

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