Water → HCID 22000416, compound

HRID 1976129Notes

Reaction equation

HRID 1976129 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10]2[S:11][C:12]3[CH2:19][CH2:18][CH2:17][C:16]4[CH:20]=[CH:21][C:22]([F:24])=[CH:23][C:15]=4[C:13]=3[N:14]=2)[CH2:5][CH2:4]1.[C:25](Cl)(=[O:27])[CH3:26].O>N1C=CC=CC=1>[F:24][C:22]1[CH:21]=[CH:20][C:16]2[CH2:17][CH2:18][CH2:19][C:12]3[S:11][C:10]([NH:9][CH:6]4[CH2:7][CH2:8][CH:3]([CH2:2][NH:1][C:25](=[O:27])[CH3:26])[CH2:4][CH2:5]4)=[N:14][C:13]=3[C:15]=2[CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 178511277HCID 178511277, compound

Product 1

HCID 22000416HCID 22000416, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred, septum capped solution of trans-N2-[4-(aminomethyl)cyclohexyl]-9-fluoro-5,6-dihydro-4H-benzo-[6,7]cyclohepta[d][1,3]thiazol-2-amine (0.165 g, 0.394 mmol) in 3.0 ml anhydrous pyridine was added 0.034 ml (0.038 g, 0.48 mmol) acetyl chloride dropwise. Stirring at room temperature was continued for 90 minutes and the solution was then poured into 50 ml water and extracted with EtOAc (2×50 ml). The combined extracts were evaporated to yield 0.126 g of the crude product as a viscous golden oil. The oil was chromatographed on preparative TLC eluting with EtOAc to yield 28% (0.042 g) of the desired product as a white solid: 1H-NMR (CDCl3) δ 1.13 (4H, m), 1.43 (1H, m), 1.80 (2H, m), 1.98 (3H,s), 2.05 (2H, m), 2.21 (2H, m), 2.80 (4H, m), 3.10 (2H, t, J=6.5 Hz), 3.24 (1H, m), 5.00 (1H, d, J=7.8 Hz), 5.75 (1H, m), 6.81 (1H, dt, J=2.8, 8.2 Hz), 7.04 (1H, m), 7.69 (1H, dd, J=2.7, 10.8 Hz); m.p. 88-91° C.

Workup

  1. extractionextracted with EtOAc (2×50 ml)
  2. customThe combined extracts were evaporated
  3. customto yield 0.126 g of the crude product as a viscous golden oil
  4. customThe oil was chromatographed on preparative TLC
  5. washeluting with EtOAc

Sources & evidence

ORD record
ord-bc53a91620ee403c96a593d565e0d8c0
Source dataset
uspto-grants-2001_05
Patent number
US06225330B1

Reaction notes

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