Triethylamine → HCID 59129275, compound

HRID 468426Notes

Reaction equation

HRID 468426 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-e7f2b7def11c4277ae5c01d1442cbba7
Source dataset
uspto-grants-2014_01
Patent number
US08623905B2

Reaction notes

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