3-Fluorobenzylamine → HCID 58055090, compound

HRID 2067996Notes

Reaction equation

HRID 2067996 reaction equation
Cl.[Cl:2][CH2:3][C:4]1[N:5]=[C:6]([NH2:9])[S:7][CH:8]=1.[C:10](C1NC=CN=1)(C1NC=CN=1)=[O:11].CCN(C(C)C)C(C)C.[F:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=1)[CH2:35][NH2:36]>C1COCC1.O>[Cl:2][CH2:3][C:4]1[N:5]=[C:6]([NH:9][C:10]([NH:36][CH2:35][C:34]2[CH:37]=[CH:38][CH:39]=[C:32]([F:31])[CH:33]=2)=[O:11])[S:7][CH:8]=1

Participants

7

Reactant 4

HCID 668533-FluorobenzylamineHCID 732282-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1)2×HCID 81531DiisopropylethylamineHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 58055090HCID 58055090, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent4×

Procedure

A stirred mixture of Intermediate 1: 4-(chloromethyl)thiazol-2-amine hydrochloride (27.8 g, 0.15 mol), carbonyl diimidazole (25.5 g, 0.157 mol), and anhydrous THF (0.2 L) was treated dropwise with a solution of DIPEA (26.2 mL, 0.15 mol) in THF (20 mL) at 20-30° C. After 2-3 hours stifling, a solution of 3-fluorobenzylamine (18.5 mL, 0.164 mol) in THF (40 mL) was added. The reaction was diluted with water (200 mL) and THF was evaporated under reduced pressure. The residue was extracted with DCM (2×200 mL). The combined extracts were dried over sodium sulfate and concentrated to leave an orange resin that was purified by silica gel chromatography (acetone/hexane) to afford Intermediate 4 as a pale yellow solid (26 g, 58% yield).

Workup

  1. customwas evaporated under reduced pressure
  2. extractionThe residue was extracted with DCM (2×200 mL)
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. concentrationconcentrated
  5. customto leave an orange resin that
  6. customwas purified by silica gel chromatography (acetone/hexane)

Sources & evidence

ORD record
ord-3f8266bca2554f539faf2dac6be40479
Source dataset
uspto-grants-2012_10
Patent number
US08293919B2

Reaction notes

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