Cyclobutanecarbonyl chloride → HCID 91195843, compound

HRID 1063179Notes

Reaction equation

HRID 1063179 reaction equation
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]([C:9]2[S:17][C:16]3[C:11](=[N:12][CH:13]=[CH:14][C:15]=3[Cl:18])[CH:10]=2)=[O:8])[CH2:3]1.[CH:19]1([C:23](Cl)=[O:24])[CH2:22][CH2:21][CH2:20]1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:18][C:15]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:10]=[C:9]([C:7]([N:4]3[CH2:5][CH2:6][CH:2]([NH:1][C:23]([CH:19]4[CH2:22][CH2:21][CH2:20]4)=[O:24])[CH2:3]3)=[O:8])[S:17][C:16]=12

Participants

5

Reactant 2

HCID 78705Cyclobutanecarbonyl chlorideHCID 22278662HCID 22278662, compound

Product 1

HCID 91195843HCID 91195843, compoundYield 70.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-amino-pyrrolidin-1-yl)-(7-chloro-thieno[3,2-b]pyridin-2yl)-methanone (0.40 g, 1.4 mmol) and DMAP (0.693 g, 5.68 mmol) in CH2Cl2 (20 mL) was added cyclobutane carboxylic acid chloride (0.20 g, 1.7 mmol). After 3 h the reaction was quenched with distilled water (10 mL). The aqueous layer was extracted with CH2Cl2 (2×10 mL). The combined organic extracts were dried (Na2SO4), and concentrated onto silica gel (5 mL). Purification by flash chromatography on silica gel (CH2Cl2/MeOH 97:3) afforded the title compound as a white solid (0.36 g, 69%). MS: 364/366 (MH+); HPLC Rf: 4.24 min; HPLC purity: 94%.

Workup

  1. customAfter 3 h the reaction was quenched with distilled water (10 mL)
  2. extractionThe aqueous layer was extracted with CH2Cl2 (2×10 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated onto silica gel (5 mL)
  5. customPurification by flash chromatography on silica gel (CH2Cl2/MeOH 97:3)

Sources & evidence

ORD record
ord-94c96b6d983f4d32a3a1a8c405b91990
Source dataset
uspto-grants-2005_11
Patent number
US06964961B2

Reaction notes

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