Sodium Bicarbonate → HCID 70978474, compound

HRID 2281077Notes

Reaction equation

HRID 2281077 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]3[CH2:14][CH2:13]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[C:15]1[CH:31]=[CH:30][C:18]([CH2:19][NH:20][C:21]([NH:23][CH2:24][C:25]([O:27]CC)=O)=[O:22])=[CH:17][CH:16]=1.C(=O)(O)[O-].[Na+]>Cl>[Cl:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]3[CH2:14][CH2:13]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[C:15]1[CH:16]=[CH:17][C:18]([CH2:19][N:20]2[C:25](=[O:27])[CH2:24][NH:23][C:21]2=[O:22])=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 71002255HCID 71002255, compound

Product 1

HCID 70978474HCID 70978474, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Ethyl N-({4-[4-chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]benzyl}carbamoyl)glycinate (Example 83, 30 mg, 0.068 mmol) was dissolved in hydrochloric acid (1.4 mL, 1 N aqueous) and placed into an oil-bath preheated at 100° C. for 1.5 hours. The mixture was cooled to ambient temperature, treated with sodium bicarbonate (aqueous saturated) and extracted with ethyl acetate (3×30 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by preparative reverse phase HPLC (85:15 to 36:64; water containing 0.1% trifluoroacetic acid:acetonitrile containing 0.1% trifluoroacetic acid) to afford the titled compound: 1H-NMR (400 MHz, d6-DMSO) δ 8.17 (1H, s); 8.00 (1H, d, J=8.5 Hz); 7.58 (1H, d, J=8.6 Hz); 7.49 (2H, d, J=8.2 Hz); 7.41 (2H, d, J=8.2 Hz); 4.67 (2H, d, J=7.2 Hz); 4.62 (2H, s); 4.02 (2H, s); 1.43-1.37 (1H, m); 0.59-0.55 (2H, m); 0.51-0.48 (2H, m) ppm; high resolution mass spectrometry (ES+) m/z 396.1242 [(M+H)+; calculated for C20H19ClN5O2: 396.1222].

Workup

  1. customplaced into an oil-bath
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. dry with materialThe combined organic extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative reverse phase HPLC (85:15 to 36:64; water containing 0.1% trifluoroacetic acid:acetonitrile containing 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-4ee2d10a264c48df9aa4be7720a8720a
Source dataset
uspto-grants-2015_09
Patent number
US09139576B2

Reaction notes

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