Methanol → (R)-N-(2-Azido-1-benzylethyl)-4-hydroxy-1-methyl-1H-indole-2-carboxamide

HRID 749315Notes

Reaction equation

HRID 749315 reaction equation
[N:1]([CH2:4][C@H:5]([NH2:13])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[N+:2]=[N-:3].O[C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]([CH3:24])[C:16]=1[C:25]([OH:27])=O.C[OH:29]>>[N:1]([CH2:4][C@H:5]([NH:13][C:25]([C:16]1[N:17]([CH3:24])[C:18]2[C:23]([CH:15]=1)=[C:22]([OH:29])[CH:21]=[CH:20][CH:19]=2)=[O:27])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[N+:2]=[N-:3]

Participants

4

Reactant 3

HCID 887MethanolHCID 14802497(R)-2-azido-1-benzylethylamineHCID 547114253-Hydroxy-1-methyl-1H-indole-2-carboxylic acid

Product 1

HCID 86601455(R)-N-(2-Azido-1-benzylethyl)-4-hydroxy-1-methyl-1H-indole-2-carboxamide

Procedure

From (R)-2-azido-1-benzylethylamine (prepared as described by Horwell, et al., J. Med. Chem., 1991, 404-414) and 4 hydroxy-1-methyl-1H-indole-2-carboxylic acid the title compound was prepared by a method analogous to that described in Example 13. MS ES (M++H)=350; [α]D=+94.8° (MeOH, C=1).

Sources & evidence

ORD record
ord-81e0566dba6b411db778eb9a23341747
Source dataset
uspto-grants-2008_07
Patent number
US07402604B2

Reaction notes

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