Cyclobutanecarbonyl chloride → HCID 59852752, compound

HRID 2373931Notes

Reaction equation

HRID 2373931 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([F:30])=[C:11]([CH:15]([C:23]2[C:28](Cl)=[N:27][CH:26]=[CH:25][N:24]=2)[NH:16][C:17]([CH:19]2[CH2:22][CH2:21][CH2:20]2)=O)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC1C(F)=C(C(N)C2C(Cl)=NC=C[N:47]=2)C=CC=1)C1C=CC=CC=1.C(N(C(C)C)CC)(C)C.C1(C(Cl)=O)CCC1>C(Cl)Cl>[NH2:47][C:28]1[C:23]2[N:24]([C:17]([CH:19]3[CH2:22][CH2:21][CH2:20]3)=[N:16][C:15]=2[C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:10]=2[F:30])[CH:25]=[CH:26][N:27]=1

Participants

6

Reactant 4

HCID 78705Cyclobutanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 57456316HCID 57456316, compoundHCID 59852781HCID 59852781, compound

Product 1

HCID 59852752HCID 59852752, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[(3-benzyloxy-2-fluorophenyl) (3-chloropyrazin-2-yl)methyl]cyclobutylcarboxamide: To a solution of C-(3-benzyloxy-2-fluoro-phenyl)-C-(3-chloro-pyrazin-2-yl)-methylamine (1.1 g, 3.2 mmole) in methylene chloride (10 mL) was added diisopropylethylamine (1.1 mL, 6.4 mmole) under a nitrogen atmosphere. The reaction mixture was cooled in an ice bath and cyclobutanecarboxylic acid chloride (0.55 mL, 4.8 mmole) was added in one portion. The reaction mixture was stirred overnight at room temperature then quenched with water (10 mL). The organic layer separated and washed with 10% aqueous NaHCO3, dried over anhydrous Na2SO4, filtered and concentrated. The crude product was purified by silica gel column chromatography using hexane:ethyl acetate (60:40) as an eluant to give the title compound (911 mg, 67%). FAB-MS: m/z 426.3 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. customthen quenched with water (10 mL)
  3. customThe organic layer separated
  4. washwashed with 10% aqueous NaHCO3
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ed17c6bafd2c4e28acd5282e13b81d89
Source dataset
uspto-grants-2008_12
Patent number
US07459554B2

Reaction notes

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