Phenyl isocyanate → 1-(2-(2-(3-(Benzyloxy)pyridin-2-ylamino)thiazol-4-yl)ethyl)-3-phenylurea

HRID 1426174Notes

Reaction equation

HRID 1426174 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.[N:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[C:25]=[O:26].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:25]([NH:24][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:26])[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

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8857Ethyl AcetateHCID 866397044-(2-aminoethyl)-N-(3-(benzyloxy)pyridin-2-yl)thiazol-2-amine

Product 1

HCID 592257051-(2-(2-(3-(Benzyloxy)pyridin-2-ylamino)thiazol-4-yl)ethyl)-3-phenylureaYield 35.8%

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 1-isocyanatobenzene (0.182 g, 1.53 mmol) was added. The reaction mixture was stirred for 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 afford the title compound (0.122 g, 35.8% yield) as a light yellow powder. 1H NMR (DMSO-d6) δ 2.75 (t, 2H), 3.42 (q, 2H), 5.27 (s, 2H), 6.19 (t, 1H), 6.70 (s, 1H), 6.86-6.91 (m, 2H), 7.20 (t, 2H), 7.34-7.43 (m, 6H), 7.58 (d, 2H), 7.87 (d, 1H), 8.48 (s, 1H), 9.94 (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-3ff81066872e44c684118f44b94ed5dc
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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