Water → HCID 22000421, compound

HRID 1976133Notes

Reaction equation

HRID 1976133 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([NH:9][C:10]2[S:11][C:12]3[CH2:19][CH2:18][O:17][C:16]4[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=4[C:13]=3[N:14]=2)[CH2:5][CH2:4]1.[C:24](Cl)(=[O:27])[CH2:25][CH3:26].O>N1C=CC=CC=1.C(N(C(C)C)CC)(C)C>[N:14]1[C:13]2[C:15]3[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=3[O:17][CH2:18][CH2:19][C:12]=2[S:11][C:10]=1[NH:9][CH:6]1[CH2:7][CH2:8][CH:3]([CH2:2][NH:1][C:24](=[O:27])[CH2:25][CH3:26])[CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 962WaterHCID 62324Propionyl chlorideHCID 20651569HCID 20651569, compound

Product 1

HCID 22000421HCID 22000421, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 81531DiisopropylethylamineSolvent

Procedure

To a stirred solution of N2-[4-(aminomethyl)cyclohexyl]-4,5-dihydrobenzo[2,3]oxepino[4,5-d][1,3]thiazol-2-amine (0.600 g, 1.49 mmol) in anhydrous pyridine (3 ml) and diisopropylethylamine (3 ml) was added propionyl chloride (0.144 ml, 1.66 mmol) dropwise. The solution was stirred for 20 minutes at room temperature and then poured into water (50 ml) and extracted with EtOAc. The solvent was removed and the residue chromatographed on silica-gel eluting with EtOAc to yield 70% (402 mg) of the product as a light yellow solid: 1H-NMR (CDCl3) δ 1.12 (6H, m), 1.50 (1H, m), 1.65 (1H, m), 1.85 (2H, d, J=12.1 Hz), 2.22 (4H, m), 3.16 (4H, t, J=5.3 Hz), 3.32 (1H, m), 4.33 (2H, t, J=5.2 Hz), 4.81 (1H, m), 5.49 (1H, m), 7.00 (1H, d, J=8.5 Hz), 7.15 (2H, m), 8.25 (1H, d, J=8.1 Hz). m.p. 56-60° C. FAB+m/z=386 (MH+).

Workup

  1. extractionextracted with EtOAc
  2. customThe solvent was removed
  3. customthe residue chromatographed on silica-gel
  4. washeluting with EtOAc

Sources & evidence

ORD record
ord-7b80f9e6527548b69e53da695833e22d
Source dataset
uspto-grants-2001_05
Patent number
US06225330B1

Reaction notes

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