Cyclobutylamine → HCID 71224013, compound

HRID 2402949Notes

Reaction equation

HRID 2402949 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:33]=[CH:34][CH:35]=1)[C:6]([C:8]1[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][N:11]=[C:10]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]3)=[CH:22][CH:21]=2)[N:9]=1)=[O:7])=O.[CH:36]1([NH2:40])[CH2:39][CH2:38][CH2:37]1.[BH3-]C#N.[Na+]>O1CCOCC1>[CH:36]1([NH:40][CH2:1][C:3]2[CH:4]=[C:5]([CH:33]=[CH:34][CH:35]=2)[C:6]([C:8]2[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][N:11]=[C:10]([NH:19][C:20]3[CH:21]=[CH:22][C:23]([N:26]4[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]4)=[CH:24][CH:25]=3)[N:9]=2)=[O:7])[CH2:39][CH2:38][CH2:37]1

Participants

5

Reactant 3

HCID 75645CyclobutylamineHCID 5003444Sodium cyanoborohydrideHCID 89388365HCID 89388365, compound

Product 1

HCID 71224013HCID 71224013, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of Example 158C (100 mg, 0.2 mmol), cyclobutanamine (30 mg, 0.4 mmol) and NaCNBH3 (13 mg, 0.2 mmol) in dioxane (5 mL) was heated at 70° C. for two days. The volatiles were removed, and the residue was purified by HPLC (Zorbax C-18, Mobile phase A: 0.1% TFA in H2O; B: 0.1% TFA in CH3CN; 0-100% gradient) to provide the title compound. MS (DCI/NH3) m/z 529 (M+H)+.

Workup

  1. customThe volatiles were removed
  2. customthe residue was purified by HPLC (Zorbax C-18, Mobile phase A: 0.1% TFA in H2O; B: 0.1% TFA in CH3CN; 0-100% gradient)

Sources & evidence

ORD record
ord-6fbc68b5e8ec4b1196adb3612937ff34
Source dataset
uspto-grants-2014_08
Patent number
US08796289B2

Reaction notes

Loading…