L-(-)-Tryptophanol → 6-Chloro-2-[(S)-1-hydroxymethyl-2-(1H-indol-3-yl)-ethylamino]-quinoline-3-carboxylic acid

HRID 2065602

Reaction equation

Cl[C:2]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:15])[CH:8]=2)[N:3]=1.[NH2:16][C@H:17]([CH2:28][OH:29])[CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1>>[Cl:15][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH:16][C@H:17]([CH2:28][OH:29])[CH2:18][C:19]1[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=1)[C:11]([C:12]([OH:14])=[O:13])=[CH:10]2

Participants

Reactant 2

HCID 6951149L-(-)-Tryptophanol

HCID 242660682,6-Dichloroquinoline-3-carboxylic acid

Product 1

HCID 452570596-Chloro-2-[(S)-1-hydroxymethyl-2-(1H-indol-3-yl)-ethylamino]-quinoline-3-carboxylic acidYield 73%

Procedure

In close analogy to the procedure described in Example 1, 2,6-dichloroquinoline-3-carboxylic acid is reacted with L-tryptophanol to provide the title compound in 73% yield as yellow needles (recrystallization from EtOH).

Sources & evidence

ORD record: ord-680c388c44044c8ea031615f829d84c2
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288549B2

Linked notes

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