Water → HCID 22000416, compound

HRID 917498Notes

Reaction equation

HRID 917498 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-b22deb26b5074bf68369afff450a6f71
Source dataset
uspto-grants-2007_09
Patent number
US07273880B2

Reaction notes

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