Benzoyl chloride → N-(2-(2-(3-(Benzyloxy)pyridin-2-ylamino)thiazol-4-yl)ethyl)benzamide

HRID 1426176Notes

Reaction equation

HRID 1426176 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[N:5]=[C:6]([NH:9][C:10]2[C:15]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:14][CH:13]=[CH:12][N:11]=2)[S:7][CH:8]=1.C(N(CC)CC)C.[C:31](Cl)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(OCC)(=O)C>CN(C=O)C>[CH2:17]([O:16][C:15]1[C:10]([NH:9][C:6]2[S:7][CH:8]=[C:4]([CH2:3][CH2:2][NH:1][C:31](=[O:38])[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[N:5]=2)=[N:11][CH:12]=[CH:13][CH:14]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 866397044-(2-aminoethyl)-N-(3-(benzyloxy)pyridin-2-yl)thiazol-2-amine

Product 1

HCID 59225640N-(2-(2-(3-(Benzyloxy)pyridin-2-ylamino)thiazol-4-yl)ethyl)benzamideYield 21.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Crude 4-(2-aminoethyl)-N-(3-(benzyloxy)pyridin-2-yl)thiazol-2-amine (Example 134, Step A; 0.25 g, 0.766 mmol) was dissolved in DMF (10 mL), and triethylamine (0.427 ml, 3.06 mmol) was added, followed by benzoyl chloride (0.215 g, 1.53 mmol). The reaction mixture was stirred 2 hours, then partitioned between ethyl acetate and water. The organic layer was washed with water and brine, dried, and concentrated. The residue was purified via MPLC (Biotage) eluting with 2:3 hexane:ethyl acetate to provide the title compound (0.072 g, 21.8% yield) as a white powder. 1H NMR (DMSO-d6) δ 2.85 (t, 2H), 3.58 (m, 2H), 5.26 (s, 2H), 6.69 (s, 1H), 6.89 (m, 1H), 7.32-7.59 (m, 9H), 7.82-7.87 (m, 3H), 8.55 (t, 1H), 9.95 (s, 1H).

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer was washed with water and brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified via MPLC (Biotage)
  6. washeluting with 2:3 hexane

Sources & evidence

ORD record
ord-5f247ca19c9d4364b0c1612072cd28cd
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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