Pyridine → HCID 46179574, compound

HRID 1886986Notes

Reaction equation

HRID 1886986 reaction equation
[CH3:1][N:2]([CH3:30])[CH2:3][CH2:4][N:5]1[C:11](=[O:12])[C@H:10]([OH:13])[C@H:9]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[S:8][C:7]2[C:22]([C:26]([O:28][CH3:29])=[O:27])=[CH:23][CH:24]=[CH:25][C:6]1=2.N1C=CC=CC=1.[C:37](Cl)(=[O:39])[CH3:38]>C(Cl)Cl>[C:37]([O:13][C@@H:10]1[C@H:9]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)[S:8][C:7]2[C:22]([C:26]([O:28][CH3:29])=[O:27])=[CH:23][CH:24]=[CH:25][C:6]=2[N:5]([CH2:4][CH2:3][N:2]([CH3:1])[CH3:30])[C:11]1=[O:12])(=[O:39])[CH3:38]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 86654322HCID 86654322, compound

Product 1

HCID 46179574HCID 46179574, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
22 °C

Procedure

To a solution of 19 mg (0.045 mmol) of (+/−)-(2S,3S)-methyl 5-(2-(dimethylamino)ethyl)-3-hydroxy-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]thiazepine-9-carboxylate in 0.5 mL of DCM was added 22 μL (0.27 mmol) of pyridine and 4 μL (0.06 mmol) of acetyl chloride. The reaction was stirred at 22° C. for 3 hours. The reaction mixture was diluted with DCM, washed sequentially with 1 M Na2CO3 and water, dried (Na2SO4), and evaporated. The residue was purified by flash chromatography on silica gel, eluting with DCM then gradually increasing to 3% methanol/DCM to give 1a. MS found M+H=473. The hydrochloride salt of 1a was recrystallized from ethyl acetate; mp 169-172° C.

Workup

  1. washwashed sequentially with 1 M Na2CO3 and water
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customThe residue was purified by flash chromatography on silica gel
  5. washeluting with DCM
  6. temperaturethen gradually increasing to 3% methanol/DCM

Sources & evidence

ORD record
ord-57507ad4efe44be699f690cf75b8dbf9
Source dataset
uspto-grants-2013_08
Patent number
US08501727B2

Reaction notes

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