Acetic Acid → HCID 178521684, compound

HRID 1694380Notes

Reaction equation

HRID 1694380 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([NH:12][C:13]([C:15]3[CH:16]=[CH:17][CH:18]=[C:19]4[C:23]=3[N:22]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=3)[CH2:21][CH2:20]4)=[O:14])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].[N:33]([Sn](CCCC)(CCCC)CCCC)=[N+:34]=[N-:35].CC(O)=O>C1(C)C=CC=CC=1>[Cl:32][C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][C:28]=1[Cl:31])[CH2:24][N:22]1[C:23]2[C:19](=[CH:18][CH:17]=[CH:16][C:15]=2[C:13]([NH:12][C:9]2([C:6]3[CH:7]=[CH:8][C:3]([C:1]4[NH:35][N:34]=[N:33][N:2]=4)=[CH:4][CH:5]=3)[CH2:11][CH2:10]2)=[O:14])[CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4984872Tributyltin azideHCID 58017575HCID 58017575, compound

Product 1

HCID 178521684HCID 178521684, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-[1-(4-cyanophenyl)cyclopropyl]-1-(3,4-dichlorobenzyl)indoline-7-carboxamide (125 mg, 0.27 mmol) and azidotributyltin (222 ul, 0.81 mmol) were refluxed in 1 ml of toluene overnight. 350 ul of AcOH was added and the resulting solid was filtered and washed with toluene. 1H NMR (500 MHz, DMSO-d6): δ 9.20 (s, 1H), 7.90 (d, 2H), 7.50 (m, 2H), 7.35 (d, 2H), 7.25 (d, 1H), 7.15 (m, 2H), 6.70 (t, 1H), 4.25 (s, 2H), 3.25 (2H), 2.95 (t, 2H), 1.20 (2H), 1.05 (m, 2H). MS−ESI (503.0).

Workup

  1. filtrationthe resulting solid was filtered
  2. washwashed with toluene

Sources & evidence

ORD record
ord-3b3b2f7307174168bade8a47c259dbdc
Source dataset
uspto-grants-2012_04
Patent number
US08158671B2

Reaction notes

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