Hydroxylamine → 2-(4-(5-((4-chlorobenzyloxy)carbamoyl)-1H-indol-1-yl)-3-cyanophenyl)acetic acid

HRID 1810105Notes

Reaction equation

HRID 1810105 reaction equation
[NH2:1][OH:2].[C:3]([C:5]1[CH:10]=[C:9]([CH2:11][C:12]([O:14]C)=[O:13])[CH:8]=[CH:7][C:6]=1[N:16]1[C:24]2[C:19](=[CH:20][C:21]([C:25]([OH:27])=O)=[CH:22][CH:23]=2)[CH:18]=[CH:17]1)#[N:4].[C:28]([Cl:33])(=O)[C:29](Cl)=O>C(N(CC)CC)C>[Cl:33][C:28]1[CH:29]=[CH:3][C:5]([CH2:10][O:2][NH:1][C:25]([C:21]2[CH:20]=[C:19]3[C:24](=[CH:23][CH:22]=2)[N:16]([C:6]2[CH:7]=[CH:8][C:9]([CH2:11][C:12]([OH:14])=[O:13])=[CH:10][C:5]=2[C:3]#[N:4])[CH:17]=[CH:18]3)=[O:27])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 65578Oxalyl chlorideHCID 685123251-(2-cyano-4-(2-methoxy-2-oxoethyl)phenyl)-1H-indole-5-carboxylic acid

Product 1

HCID 595499292-(4-(5-((4-chlorobenzyloxy)carbamoyl)-1H-indol-1-yl)-3-cyanophenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

O-chlorobenzyl)hydroxylamine was reacted with 1-(2-cyano-4-(2-methoxy-2-oxoethyl)phenyl)-1H-indole-5-carboxylic acid in the presence of triethylamine and oxalyl chloride according to the method of Example 5, Step E, to provide 2-(4-(5-((4-chlorobenzyloxy)carbamoyl)-1H-indol-1-yl)-3-cyanophenyl)acetic acid. 1H NMR (400 MHz, CD3OD) δ 8.10 (s, 1H), 7.91 (s, 1H), 7.80 (d, J=8.6 Hz, 1H), 7.56-7.64 (m, 3H), 7.50 (d, J=8.7 Hz, 2H), 7.41 (d, J=8.6 Hz, 2H), 7.33 (d, J=8.5 Hz, 1H), 6.85 (d, J=4.1 Hz, 1H), 4.98 (s, 2H), 3.81 (s, 2H).

Sources & evidence

ORD record
ord-479750fcc4a64094b1fe760232132057
Source dataset
uspto-grants-2013_01
Patent number
US08362056B2

Reaction notes

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