Pyridine → HCID 68906352, compound

HRID 736356Notes

Reaction equation

HRID 736356 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]=[C:9]=[O:10].C([C:14]1[C:15]2[C:23]([C:24]([C:26]3[CH:31]=[C:30]([O:32][CH3:33])[N:29]=[C:28]([NH2:34])[CH:27]=3)=[O:25])=[CH:22][NH:21][C:16]=2[N:17]=[C:18]([NH2:20])[N:19]=1)(C)C.N1C=C[CH:38]=[CH:37][CH:36]=1>>[NH2:19][C:14]1[C:15]2[C:23]([C:24]([C:26]3[CH:31]=[C:30]([O:32][CH3:33])[N:29]=[C:28]([NH:34][C:9]([NH:8][C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[F:1])=[O:10])[CH:27]=3)=[O:25])=[CH:22][N:21]([CH:37]([CH3:38])[CH3:36])[C:16]=2[N:17]=[CH:18][N:20]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 855882-Fluorophenyl isocyanateHCID 68903464HCID 68903464, compound

Product 1

HCID 68906352HCID 68906352, compoundYield 93%

Procedure

1-Fluoro-2-isocyanato-benzene (0.04 mL, 0.37 mmol) was added to a solution of (4-isopropyl-Amino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(2-amino-6-methoxy-pyridin-4-yl)-methanone (0.10 g, 0.31 mmol) in pyridine (2 mL) and stirred in a sealed tube for 2 h at room temperature. The reaction mixture was quenched with water (100 mL) and extracted with hot EtOAc/MeOH (95:5, 3×100 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash column chromatography (ethyl acetate/MeOH 99:1) afforded the title compound as a yellow solid (132 mg, 93%). MS: 464.2 (MH+); HPLC Rf: 1.7 min. (HPLC method 2); HPLC purity: 100%.

Workup

  1. customThe reaction mixture was quenched with water (100 mL)
  2. extractionextracted with hot EtOAc/MeOH (95:5, 3×100 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash column chromatography (ethyl acetate/MeOH 99:1)

Sources & evidence

ORD record
ord-4226d7facfd143dca925af8f84fd3ddb
Source dataset
uspto-grants-2009_09
Patent number
US07595325B2

Reaction notes

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