Acetic Acid → 4-(1H-Imidazol-2-ylmethyl)-1-(phenylsulfonyl)-1,3,4,5-tetrahydropyrrolo[4,3,2-de]isoquinoline bis(trifluoroacetate)

HRID 1096484Notes

Reaction equation

HRID 1096484 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=O.CC(O)=O.[C:12]1([S:18]([N:21]2[C:31]3[C:32]4[C:23]([CH2:24][NH:25][CH2:26][C:27]=4[CH:28]=[CH:29][CH:30]=3)=[CH:22]2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34]>C1COCC1.CC#N>[F:36][C:35]([F:38])([F:37])[C:33]([OH:39])=[O:34].[F:36][C:35]([F:38])([F:37])[C:33]([OH:39])=[O:34].[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:25]1[CH2:24][C:23]2=[CH:22][N:21]([S:18]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)(=[O:19])=[O:20])[C:31]3[C:32]2=[C:27]([CH:28]=[CH:29][CH:30]=3)[CH2:26]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6422Trifluoroacetic acidHCID 249551H-imidazole-2-carbaldehydeHCID 250721821-(Phenylsulfonyl)-1,3,4,5-tetrahydropyrrolo[4,3,2-de]isoquinoline

Product 1

HCID 866249824-(1H-Imidazol-2-ylmethyl)-1-(phenylsulfonyl)-1,3,4,5-tetrahydropyrrolo[4,3,2-de]isoquinoline bis(trifluoroacetate)

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

The experimental for Example 2 was followed using 1H-imidazole-2-carbaldehyde (16 mg, 0.18 mmol), AcOH (46 μL, 0.81 mmol), Na(OAc)3BH3 (51 mg, 0.24 mmol) and 1-(phenylsulfonyl)-1,3,4,5-tetrahydropyrrolo[4,3,2-de]isoquinoline, Example 1 (27 mg, 0.08 mmol) in dry THF (4 mL). Preparative HPLC (YMC column 150×30 mm, 32-62% MeCN, 0.1% TFA). This gave 1.7 mg of the title compound, as a brown gum. MS m/z 379 [M+H]+.

Sources & evidence

ORD record
ord-b31472ff9fd04b2ba3fe732edaa36992
Source dataset
uspto-grants-2012_03
Patent number
US08138333B2

Reaction notes

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