Triethylamine → HCID 86628277, compound

HRID 21174Notes

Reaction equation

HRID 21174 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:34].C(N(CC)CC)C.[CH3:42][N:43]1[C:48]2[CH:49]=[CH:50][C:51]([S:53](Cl)(=[O:55])=[O:54])=[CH:52][C:47]=2[O:46][CH2:45][CH2:44]1>C(#N)C>[CH3:42][N:43]1[C:48]2[CH:49]=[CH:50][C:51]([S:53]([O:1][C:2]3[CH:10]=[CH:9][C:8]([C:11]4[N:12]([C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])[C:13]5[C:18]([CH:19]=4)=[CH:17][C:16]([CH2:20][N:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:15][CH:14]=5)=[C:7]4[C:3]=3[CH2:4][NH:5][C:6]4=[O:34])(=[O:55])=[O:54])=[CH:52][C:47]=2[O:46][CH2:45][CH2:44]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27764034-Methyl-3,4-dihydro-2h-1,4-benzoxazine-7-sulfonyl chlorideHCID 684932224-Hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

Product 1

HCID 86628277HCID 86628277, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a similar manner to Step 1 of Example 233, 4-hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (0.0324 g, 0.0702 mmol) was dissolved in acetonitrile (0.650 mL), and the solution was treated with triethylamine (0.0590 mL, 0.421 mmol) and 3,4-dihydro-4-methyl-1,4-benzoxazine-7-sulfonyl chloride (0.0520 g, 0.211 mmol) to obtain 4-(3,4-dihydro-4-methyl-1,4-benzoxazin-7-ylsulfonyloxy)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (0.0274 g, yield 58%).

Sources & evidence

ORD record
ord-a5be8521e3d040859d3dffe425a1ebd9
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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