HCID 24890015, compound → HCID 68551094, compound

HRID 2242385Notes

Reaction equation

HRID 2242385 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:10][NH2:11])[CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[C:12]([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]([F:34])([F:33])[F:32])[CH:25]=1)[C:18]([C:35](O)=[O:36])=[CH:17]2)#[N:13].OCC1(CNC(C2N(CC3C=CC=C(OC(F)(F)F)C=3)C3C(C=2)=CC(C#N)=CC=3)=O)CCCC1>>[CH2:1]([O:3][C:4]([C:6]1([CH2:10][NH:11][C:35]([C:18]2[N:19]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]([F:34])([F:32])[F:33])[CH:25]=3)[C:20]3[C:16]([CH:17]=2)=[CH:15][C:14]([C:12]#[N:13])=[CH:22][CH:21]=3)=[O:36])[CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 24890015HCID 24890015, compoundHCID 45122079Ethyl 1-(aminomethyl)cyclobutanecarboxylateHCID 685431065-cyano-1-(3-trifluoromethoxybenzyl)-1H-indole-2-carboxylic acid

Product 1

HCID 68551094HCID 68551094, compoundYield 52.2%

Procedure

1-({[5-Cyano-1-(3-trifluoromethoxybenzyl)-1H-indole-2-carbonyl]amino}methyl)-cyclobutanecarboxylic acid ethyl ester was prepared from 1-aminomethyl-cyclobutanecarboxylic acid ethyl ester (262 mg, 1.65 mmol) and 5-cyano-1-(3-trifluoromethoxybenzyl)-1H-indole-2-carboxylic acid (400 mg, 1.10 mmol) in the same manner as 5-cyano-1-(3-trifluoromethoxybenzyl)-1H-indole-2-carboxylic acid (1-hydroxymethyl-cyclopentylmethyl)amide giving 1-({[5-cyano-1-(3-trifluoromethoxybenzyl)-1H-indole-2-carbonyl]amino}methyl)cyclobutanecarboxylic acid ethyl ester as a colourless gum (287 mg, 50%).

Sources & evidence

ORD record
ord-4c89a782087e45c3a28754416f233900
Source dataset
uspto-grants-2010_03
Patent number
US07671080B2

Reaction notes

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