Dichloromethane → HCID 18446643, compound

HRID 1269052Notes

Reaction equation

HRID 1269052 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19](S(C)=O)[N:18]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:4][N:3]=1.[CH:26]1([NH2:29])[CH2:28][CH2:27]1.ClCCl>CC(C)=O>[CH:26]1([NH:29][C:19]2[N:18]=[C:17]([C:16]3[C:8]([C:6]4[CH:5]=[CH:4][N:3]=[C:2]([F:1])[CH:7]=4)=[N:9][N:10]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=34)[CH:22]=[CH:21][N:20]=2)[CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 69828CyclopropylamineHCID 18446603HCID 18446603, compound

Product 1

HCID 18446643HCID 18446643, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2-(2-fluoro-4-pyridinyl)-3-[2-(methylsulfinyl)-4-pyrimidinyl]pyrazolo[1,5-a]pyridine (430 mg, 90%, ˜1.1 mmol) in cyclopropylamine (4 mL, 57.7 mmol) was heated at 45° C. in a sealed glass tube for 6 hours. The excess cyclopropylamine was removed in vacuo to provide crude N-cyclopropyl-4-[2-(2-fluoro-4-pyridinyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinamine (370 mg, 97%). A small portion of the crude material was chromatographed (19:1 dichloromethane:acetone to 9:1 dichloromethane:acetone) to provide material as a light yellow solid. Rf 0.26 (9:1 dichloromethane:acetone); 1H NMR (CDCl3) δ 8.52 (d, 1H), 8.42 (d, 1H), 8.29 (d, 1H). 8.21 (d, 1H), 7.51 (d, 1H), 7.36 (d, 1H), 7.32 (s, 1H), 6.98 (t, 1H), 6.48 (d, 1H), 5.69 (br, 1H), 2.81 (m, 1H), 0.83 (m, 2H), 0.61 (m, 2H); MS m/z 347 (M+1).

Workup

  1. customThe excess cyclopropylamine was removed in vacuo
  2. customto provide crude N-cyclopropyl-4-[2-(2-fluoro-4-pyridinyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinamine (370 mg, 97%)
  3. customA small portion of the crude material was chromatographed (19:1 dichloromethane:acetone to 9:1 dichloromethane:acetone)
  4. customto provide material as a light yellow solid

Sources & evidence

ORD record
ord-1eb93ef8085040868ac0db5012569559
Source dataset
uspto-grants-2007_04
Patent number
US07199120B2

Reaction notes

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