Phenyl isocyanate → HCID 67374575, compound

HRID 1253491Notes

Reaction equation

HRID 1253491 reaction equation
[CH3:1][O:2][C:3]1[C:4]2[N:5]([N:15]=[CH:16][C:17]=2[C:18]#[C:19][C:20]2[CH:25]=[CH:24][N:23]=[C:22]([NH2:26])[CH:21]=2)[CH:6]=[C:7]([C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)[CH:8]=1.[C:27]1([N:33]=[C:34]=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>ClCCl>[CH3:1][O:2][C:3]1[C:4]2[N:5]([N:15]=[CH:16][C:17]=2[C:18]#[C:19][C:20]2[CH:25]=[CH:24][N:23]=[C:22]([NH:26][C:34]([NH:33][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:35])[CH:21]=2)[CH:6]=[C:7]([C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)[CH:8]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 584047124-{[4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]ethynyl}pyridin-2-amine

Product 1

HCID 67374575HCID 67374575, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{[4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]ethynyl}pyridin-2-amine (24 mg, 0.07 mmol) in dichloromethane (1400 μl) was added phenyl isocyanate (9.09 μl, 0.084 mmol) and the mixture was allowed to stir for 72 hours at room temperature. The precipitated solid was filtered was filtered and the washed with 10 mL of dichloromethane. The solid was dried in vacuo to afford N-(4-{[4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]ethynyl}pyridin-2-yl)-N′-phenylurea. 1H NMR (500 MHz, DMSO-d6) δ 10.28 (s, 1H); 9.46 (s, 1H); 8.69 (s, 1H); 8.28 (s, 1H); 8.23-8.21 (m, 2H); 8.01 (s, 1H); 7.56 (s, 1H); 7.47 (d, 2H); 7.26 (t, 2H); 7.04 (s, 1H); 6.98-6.96 (m, 2H); 4.05 (s, 3H); 3.82 (s, 3H). LRMS (ESI) calculated for C26H21N7O2 [M+H]+, 464.2; found 464.1.

Workup

  1. filtrationThe precipitated solid was filtered
  2. filtrationwas filtered
  3. washthe washed with 10 mL of dichloromethane
  4. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-bc42afbcc1fb41cab9c8af1820a5e8f5
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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