Triethylamine → HCID 59129275, compound

HRID 1847825Notes

Reaction equation

HRID 1847825 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13](Cl)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.[NH2:16][C:17]1[CH:18]=[C:19]2[C:23](=[C:24]([C:26]([O:28][CH3:29])=[O:27])[CH:25]=1)[NH:22][C:21]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:20]2.C(N(CC)CC)C>CN(C)C=O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:16][C:17]4[CH:18]=[C:19]5[C:23](=[C:24]([C:26]([O:28][CH3:29])=[O:27])[CH:25]=4)[NH:22][C:21]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:20]5)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 591291541-(Benzo[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chlorideHCID 59129322HCID 59129322, compound

Product 1

HCID 59129275HCID 59129275, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(Benzo[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chloride (45 mg, 0.20 mmol) and methyl 5-amino-2-tert-butyl-1H-indole-7-carboxylate (49.3 mg, 0.200 mmol) were dissolved in N,N-dimethylformamide (2 mL) containing a magnetic stir bar and triethylamine (0.084 mL, 0.60 mmol). The resulting solution was allowed to stir for 10 minutes at room temperature. The crude product was then purified by preparative HPLC using a gradient of 0-99% acetonitrile in water containing 0.05% trifluoroacetic acid to yield methyl 5-(1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarbox-amido)-2-tert-butyl-1H-indole-7-carboxylate. ESI-MS m/z calc. 434.2. found 435.5. (M+1)+. Retention time of 2.12 minutes.

Workup

  1. additioncontaining a magnetic stir bar
  2. customThe crude product was then purified by preparative HPLC

Sources & evidence

ORD record
ord-553f7b84daa94169950b30acd51d672b
Source dataset
uspto-grants-2015_02
Patent number
US08952049B2

Reaction notes

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