4-Chlorophenyl Isocyanate → 1-(4-chlorophenyl)-3-{5-[(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)carbonyl]pyridin-3-yl}urea

HRID 82101

Reaction equation

HRID 82101 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:13]=[C:14]([C:18]([C:20]2[C:28]3[CH:27]=[N:26][CH:25]=[N:24][C:23]=3[N:22]([CH3:29])[CH:21]=2)=[O:19])[CH:15]=[N:16][CH:17]=1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[N:16][CH:15]=[C:14]([C:18]([C:20]3[C:28]4[CH:27]=[N:26][CH:25]=[N:24][C:23]=4[N:22]([CH3:29])[CH:21]=3)=[O:19])[CH:13]=2)=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 70817432(5-aminopyridin-3-yl)(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanone

Product 1

HCID 708177141-(4-chlorophenyl)-3-{5-[(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)carbonyl]pyridin-3-yl}ureaYield 49%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-chloro-4-isocyanatobenzene (24 mg, 0.15 mmol) was added to (5-aminopyridin-3-yl)(7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanone (30 mg, 0.12 mmol) (Preparation 232) in pyridine (1.0 mL). The mixture was stirred at room temperature overnight then evaporated in vacuo to yield the product as a crude residue. The crude residue was purified by preparative HPLC to afford the title compound in 49% yield, 24 mg.

Workup

  1. customthen evaporated in vacuo
  2. customto yield the product as a crude residue
  3. customThe crude residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-a46e4832d3ab403e905d00339112dd82
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Linked notes

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