Water → HCID 22000430, compound

HRID 1976140Notes

Reaction equation

HRID 1976140 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][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)[CH2:4][CH2:3]1.[C:24](Cl)(=[O:26])[CH3:25].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][CH2:8][CH:5]1[CH2:6][CH2:7][CH:2]([NH:1][C:24](=[O:26])[CH3:25])[CH2:3][CH2:4]1

Participants

6

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 22000425HCID 22000425, compound

Product 1

HCID 22000430HCID 22000430, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 81531DiisopropylethylamineSolvent

Procedure

To a stirred solution of N2-[(4-aminocyclohexyl)methyl]-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 was added acetyl chloride (0.130 ml, 1.83 mmol) dropwise. The solution was stirred for 30 minutes at room temperature and then poured into water (60 ml). The mixture was extracted with EtOAc, and the organic phase evaporated to afford a residue that was chromatographed on silica-gel eluting with EtOAc to yield 72% (400 mg) of the desired product as a light yellow solid: m.p. 69-72° C. 1H-NMR (CDCl3) δ 1.11 (4H, m), 1.60 (1H, broad), 1.73 (1H, broad), 1.83 (2H, m), 1.95 (3H, s), 2.05 (2H, m), 3.14 (4H, m), 3.73 (1H, broad), 4.33 (2H, t, J=4.9 Hz), 5.30 (1H, broad), 7.00 (1H, dd, J=0.9 Hz, 7.7 Hz), 7.12 (2H, m), 8.24 (1H, dd, J=0.9 Hz, 7.8 Hz). ESIMS m/z=372 (MH+).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. customthe organic phase evaporated
  3. customto afford a residue that
  4. customwas chromatographed on silica-gel
  5. washeluting with EtOAc

Sources & evidence

ORD record
ord-b35c31f53ad5451e9786ca1653778fa6
Source dataset
uspto-grants-2001_05
Patent number
US06225330B1

Reaction notes

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