Water → HCID 22000389, compound

HRID 917508Notes

Reaction equation

HRID 917508 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: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][CH2:8][CH:5]1[CH2:6][CH2:7][CH:2]([NH:1][C:24](=[O:27])[CH2:25][CH3:26])[CH2:3][CH2:4]1

Participants

6

Reactant 3

HCID 962WaterHCID 62324Propionyl chlorideHCID 22000425HCID 22000425, compound

Product 1

HCID 22000389HCID 22000389, compoundYield 74%

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 (3 ml) was added propionyl chloride (0.155 ml, 1.78 mmol) dropwise. The solution was stirred for 1 hour at room temperature and poured into water (60 ml). The solution was extracted with EtOAc and the solvent removed in vacuo to yield a viscous golden oil. The oil was chromatographed on silica-gel eluting with 70% EtOAc/30% hexane to yield 74% (425 mg) of an orange solid: m.p. 70-73° C. 1H-NMR (CDCl3) δ 1.10 (6H, m), 1.60 (1H, broad), 1.83 (3H, m), 2.00 (3H, m), 2.17 (2H, q, J=7.6 Hz), 3.13 (4H, q, J=5.1 Hz), 3.73 (1H, broad), 4.32 (2H, t, J=5.3 Hz), 5.32 (1H, broad), 7.00 (1H, dd, J=6.4 Hz). ESIMS m/z=386 (MH+).

Workup

  1. extractionThe solution was extracted with EtOAc
  2. customthe solvent removed in vacuo
  3. customto yield a viscous golden oil
  4. customThe oil was chromatographed on silica-gel
  5. washeluting with 70% EtOAc/30% hexane

Sources & evidence

ORD record
ord-873ed3f29a574d1b8355d17f86ea4cf9
Source dataset
uspto-grants-2007_09
Patent number
US07273880B2

Reaction notes

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