m-Tolyl isocyanate → HCID 178425600, compound

HRID 432241Notes

Reaction equation

HRID 432241 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[N:14][C:15]=3[NH2:17])[N:10]([C@H:18]3[CH2:23][CH2:22][C@@H:21]([N:24]4[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]4)[CH2:20][CH2:19]3)[N:9]=2)=[CH:4][CH:3]=1.[C:31]1([CH3:40])[CH:36]=[CH:35][CH:34]=[C:33]([N:37]=[C:38]=[O:39])[CH:32]=1>N1C=CC=CC=1>[NH2:17][C:15]1[N:14]=[CH:13][N:12]=[C:11]2[N:10]([C@H:18]3[CH2:23][CH2:22][C@@H:21]([N:24]4[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]4)[CH2:20][CH2:19]3)[N:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:38]([NH:37][C:33]4[CH:34]=[CH:35][CH:36]=[C:31]([CH3:40])[CH:32]=4)=[O:39])=[CH:7][CH:6]=3)[C:16]=12

Participants

4

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 178480983HCID 178480983, compound

Product 1

HCID 178425600HCID 178425600, compoundYield 301.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

cis-3-(4-Aminophenyl)-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (50 mg, 0.123 mmol) was dissolved in pyridine (3.5 mL) then cooled to 0° C. m-Tolylisocyanate (18 mg, 0.135 mmol) was added and the reaction was allowed to warm to room temperature over 16 hours. The reaction mixture was concentrated under reduced pressure to yield a pale yellow oil (200 mg). Purification was achieved by RP-HPLC (Waters PrepLC 4000, flow rate: 10 mL/min. λ=254 nm Gradient: 10% to 30% acetonitrile/0.1M aqueous ammonium acetate gradient over 40 minutes; Deltapak C18, 300A, 15 μm, 40×100 mm column). The desired product was collected as a white solid (52 mg). HPLC-RT: 12.58 min. (flow rate: 1 mL/min λ=254 nm Gradient: 5% to 85% acetonitrile/0.1M aqueous ammonium acetate gradient over 20 min.; Deltapak C18, 300A, 5 μm, 150×3.9 mm column); m/z (MH+)=540.1.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-86c500f90f40444db63cac1fcbe14c2f
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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