4-Chloro-2-methylphenyl isocyanate → HCID 11648354, compound

HRID 736337

Reaction equation

HRID 736337 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[C:4]([CH3:11])[CH:3]=1.[NH2:12][C:13]1[C:14]2[C:21]([C:22]([C:24]3[CH:25]=[N:26][CH:27]=[C:28]([NH2:30])[CH:29]=3)=[O:23])=[CH:20][N:19]([CH:31]([CH3:33])[CH3:32])[C:15]=2[N:16]=[CH:17][N:18]=1>N1C=CC=CC=1>[NH2:12][C:13]1[C:14]2[C:21]([C:22]([C:24]3[CH:29]=[C:28]([NH:30][C:9]([NH:8][C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=4[CH3:11])=[O:10])[CH:27]=[N:26][CH:25]=3)=[O:23])=[CH:20][N:19]([CH:31]([CH3:33])[CH3:32])[C:15]=2[N:16]=[CH:17][N:18]=1

Participants

4

Reactant 2

HCID 1421574-Chloro-2-methylphenyl isocyanateHCID 68903795HCID 68903795, compound

Product 1

HCID 11648354HCID 11648354, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
45 °C

Procedure

4-Chloro-1-isocyanato-2-methyl-benzene (93.3 mg, 0.56 mmol) was added to a solution of (4-Amino-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(5-amino-pyridin-3-yl)-methanone (150 mg, 0.51 mmol) in pyridine (5 mL). The mixture was heated to 45° C. for 12 h. The reaction mixture was concentrated in vacuo and the resulting yellow solid was triturated with CH2Cl2, filtered, and washed with CH2Cl2. Purification by flash column chromatography [(10% NH4OH/MeOH)/ethyl acetate 2:98] afforded the title compound as a white solid (197 mg, 83%). MS: 464.1 (MH+); HPLC Rf: 5.55 min. (HPLC method 4).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resulting yellow solid was triturated with CH2Cl2
  3. filtrationfiltered
  4. washwashed with CH2Cl2
  5. customPurification by flash column chromatography [(10% NH4OH/MeOH)/ethyl acetate 2:98]

Sources & evidence

ORD record
ord-2005108721c4467896be0ffb4794ac91
Source dataset
uspto-grants-2009_09
Patent number
US07595325B2

Linked notes

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