1-Pyrrolidineethanamine → HCID 15407405, compound

HRID 1415693Notes

Reaction equation

HRID 1415693 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]1[C:12]([C:16]([OH:18])=O)=[CH:13][CH:14]=[CH:15][N:6]1[C:5]2=[O:19].[NH2:20][CH2:21][CH2:22][N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1.C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(=O)(O)[O-].[Na+].ClCCl>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]1[C:12]([C:16]([NH:20][CH2:21][CH2:22][N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[O:18])=[CH:13][CH:14]=[CH:15][N:6]1[C:5]2=[O:19]

Participants

7

Reactant 4

HCID 13441-PyrrolidineethanamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 11824685HCID 11824685, compound

Product 1

HCID 15407405HCID 15407405, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a room temperature solution of 2-iodo-11-oxo-11H-pyrido[2,1-b]quinazoline-6-carboxylic acid (2.0 g; 4.97 mmol), 1-(2-aminoethyl)pyrrolidine (1.26 ml; 9.94 mmol), N,N-diisopropylethylamine (4.33 ml; 24,8 mmol), and dichloromethane (50 ml) was added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (3.3 g; 7.45 mmol) in one portion. After a stirring period of 66 hours, the reaction mixture was diluted with half-saturated sodium bicarbonate (100 ml) and extracted with dichloromethane (3×50 ml). The combined organic phases were washed with brine (70 ml), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by repeated flash chromatography. The first purification on silica gel (250 g; elution with 10% methanol/chloroform) was followed by a second purification (250 g silica gel; elution with 45% methanol/ethyl acetate followed by a gradient elution with 10-20% methanol/chloroform) to provide product as a bright lemon yellow solid: 1.82 g.

Workup

  1. extractionextracted with dichloromethane (3×50 ml)
  2. washThe combined organic phases were washed with brine (70 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by repeated flash chromatography
  7. customThe first purification on silica gel (250 g; elution with 10% methanol/chloroform)
  8. customwas followed by a second purification (250 g silica gel
  9. washelution with 45% methanol/ethyl acetate
  10. washfollowed by a gradient elution with 10-20% methanol/chloroform)
  11. customto provide product as a bright lemon yellow solid

Sources & evidence

ORD record
ord-acf63d275e164b7ca93a95e18a8a7e32
Source dataset
uspto-grants-1999_06
Patent number
US05908840

Reaction notes

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