1-Butoxy-4-isocyanatobenzene → 3-(4-Butoxy-phenyl)-1-ethyl-1-(2-mercapto-thiazolo[5,4-b]pyridin-5-yl)-urea

HRID 1640040Notes

Reaction equation

HRID 1640040 reaction equation
[CH2:1]([NH:3][C:4]1[N:9]=[C:8]2[S:10][C:11]([SH:13])=[N:12][C:7]2=[CH:6][CH:5]=1)[CH3:2].[CH2:14]([O:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]=[O:27])=[CH:21][CH:20]=1)[CH2:15][CH2:16][CH3:17]>N1C=CC=CC=1>[CH2:14]([O:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:27])[N:3]([CH2:1][CH3:2])[C:4]2[N:9]=[C:8]3[S:10][C:11]([SH:13])=[N:12][C:7]3=[CH:6][CH:5]=2)=[CH:21][CH:20]=1)[CH2:15][CH2:16][CH3:17]

Participants

4

Reactant 2

HCID 27696291-Butoxy-4-isocyanatobenzeneHCID 1784632545-Ethylamino-thiazolo[5,4-b]pyridine-2-thiol

Product 1

HCID 1784501953-(4-Butoxy-phenyl)-1-ethyl-1-(2-mercapto-thiazolo[5,4-b]pyridin-5-yl)-ureaYield 13.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Into 13×100 mm pyrex reaction vial were added 5-ethylamino-thiazolo[5,4-b]pyridine-2-thiol (105 mg, 0.49 mmol), anhydrous pyridine (2 ml), and 4-butoxyphenyl isocyanate (135 μl, 0.74 mmol). The reaction mixture was stirred 3.5 h, then concentrated. Purification by preparative TLC (40% EtoAc in Hexanes) gave 26 mg (13%) of the title compound. 1H NMR (DMSO-d6) δ=0.91 (t, 3H), 1.10 (t, 3H), 1.39 (m, 2H), 1.61 (m, 2H), 3.91 (m, 1H), 6.80 (d, 2H), 7.30 (m, 3H), 7.99 (br d, 1H), 9.43 (s, 1H); ESIMS: m/z 401 (M−H); mp 134.3-135 C.

Workup

  1. customreaction
  2. concentrationconcentrated
  3. customPurification by preparative TLC (40% EtoAc in Hexanes)

Sources & evidence

ORD record
ord-6b133a58e31c4f06aa6dee96175965c3
Source dataset
uspto-grants-2012_02
Patent number
US08110686B2

Reaction notes

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