Triethylamine → HCID 58309297, compound

HRID 537637Notes

Reaction equation

HRID 537637 reaction equation
[CH2:1]([N:3]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:16]3[O:17][C:18]4([C:28]([CH3:30])([CH3:29])[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[N:21]4[CH3:31])[CH:19]=[N:20][C:15]=3[CH:14]=2)=[CH:9][CH:8]=1)[CH2:4][CH2:5][OH:6])[CH3:2].C(N(CC)CC)C.[C:45](Cl)(=[O:48])[CH2:46][CH3:47]>C(Cl)Cl>[C:45]([O:6][CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:16]3[O:17][C:18]4([C:28]([CH3:29])([CH3:30])[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[N:21]4[CH3:31])[CH:19]=[N:20][C:15]=3[CH:14]=2)=[CH:9][CH:8]=1)(=[O:48])[CH2:46][CH3:47]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 498451142-(Ethyl(4-(1,3,3-trimethylspiro[indoline-2,2'-naphtho[1,2-b][1,4]oxazine]-6'-yl)phenyl)amino)ethanol

Product 1

HCID 58309297HCID 58309297, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(ethyl(4-(1,3,3-trimethylspiro[indoline-2,2′-naphtho[1,2-b][1,4]oxazine]-6′-yl)phenyl)amino)ethanol (Example 8, Step 3) (0.085 g, 0.17 mmol) in DCM (5 ml) was treated with triethylamine (0.026 g, 0.26 mmol) in one portion followed by propionyl chloride (0.019 g, 0.21 mmol) and stirred at RT for 18 hrs. The solvent was then evaporated in vacuo and the crude residue purified by column chromatography (silica gel) eluting with 0-10% EtOAc/Petroleum ether, which gave the pure product, 2-(ethyl(4-(1,3,3-trimethylspiro[indoline-2,2′-naphtho[1,2-b][1,4]oxazine]-6′-yl)phenyl)amino)ethyl propionate, as a pale green foam upon evaporation of the solvent in vacuo (0.08 g, 84%).

Workup

  1. customThe solvent was then evaporated in vacuo
  2. customthe crude residue purified by column chromatography (silica gel)
  3. washeluting with 0-10% EtOAc/Petroleum ether, which

Sources & evidence

ORD record
ord-ba69668449f44a2d9903c9e0b993ed95
Source dataset
uspto-grants-2014_10
Patent number
US08865029B2

Reaction notes

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