Benzene, 1-chloro-3-isocyanato- → 1-(3-Chloro-phenyl)-3-{5-[2-(6-cyano-thieno[3,2-b]pyridin-7-ylamino)-ethyl]-thiazol-2-yl}-urea

HRID 1468996Notes

Reaction equation

HRID 1468996 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH2:7][CH2:8][NH:9][C:10]2[C:15]([C:16]#[N:17])=[CH:14][N:13]=[C:12]3[CH:18]=[CH:19][S:20][C:11]=23)=[CH:5][N:6]=1.[Cl:21][C:22]1[CH:23]=[C:24]([N:28]=[C:29]=[O:30])[CH:25]=[CH:26][CH:27]=1>ClCCl>[Cl:21][C:22]1[CH:23]=[C:24]([NH:28][C:29]([NH:1][C:2]2[S:3][C:4]([CH2:7][CH2:8][NH:9][C:10]3[C:15]([C:16]#[N:17])=[CH:14][N:13]=[C:12]4[CH:18]=[CH:19][S:20][C:11]=34)=[CH:5][N:6]=2)=[O:30])[CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 17968Benzene, 1-chloro-3-isocyanato-HCID 866405207-[2-(2-Amino-thiazol-5-yl)-ethylamino]-thieno[3,2-b]pyridine-6-carbonitrile

Product 1

HCID 451376951-(3-Chloro-phenyl)-3-{5-[2-(6-cyano-thieno[3,2-b]pyridin-7-ylamino)-ethyl]-thiazol-2-yl}-ureaYield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-[2-(2-amino-thiazol-5-yl)-ethylamino]-thieno[3,2-b]pyridine-6-carbonitrile (27.1 mg, 0.09 mmol) in 2 ml of dichloromethane was added 3-chloro phenyl isocyanate (0.02 ml, 0.16 mmol). The resulting mixture was stirred at room temperature for 16 hr and filtered. Solids were washed with CH2Cl2, and the combined organics were concentrated. The residue was purified by chromatography on TLC plate with MeOH/CH2Cl2/NH3(aq)=1/20/0.1 to give 5.6 mg (14%) of a white solid. 1H NMR (400 MHz, CD3OD) δ 8.41 (s, 1H), 8.06 (d, J=5.6 Hz, 1H), 7.62-7.66 (m, 1H), 7.43 (d, J=5.2 Hz, 1H), 7.25-7.31 (m, 2H), 7.16 (s, 1H), 7.00-7.07 (m, 1H), 4.06 (t, J=7.2 Hz, 2H), 3.20 (t, J=7.2 Hz, 2H). LC-MS (ESI) m/z 455.0 (M+1).

Workup

  1. filtrationfiltered
  2. washSolids were washed with CH2Cl2
  3. concentrationthe combined organics were concentrated
  4. customThe residue was purified by chromatography on TLC plate with MeOH/CH2Cl2/NH3(aq)=1/20/0.1

Sources & evidence

ORD record
ord-0f25cd0373ed4d01bf633dd7bff75804
Source dataset
uspto-grants-2015_04
Patent number
US09006252B2

Reaction notes

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