6-Methyl-4-pyridazinecarboxylic acid hydrochloride → [(3R,4S)-3-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(5-chloro-pyridin-2-yloxy)-ethyl]-4-(3,4-difluoro-phenyl)-pyrrolidin-1-yl]-(6-methyl-pyridazin-4-yl)-methanone

HRID 906945Notes

Reaction equation

HRID 906945 reaction equation
[C:1]([Si:5]([CH3:31])([CH3:30])[O:6][CH2:7][C@@H:8]([C@@H:17]1[C@@H:21]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[C:24]([F:29])[CH:23]=2)[CH2:20][NH:19][CH2:18]1)[O:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:32][C:33]1[N:38]=[N:37][CH:36]=[C:35]([C:39](O)=[O:40])[CH:34]=1>>[C:1]([Si:5]([CH3:31])([CH3:30])[O:6][CH2:7][C@@H:8]([C@@H:17]1[C@@H:21]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[C:24]([F:29])[CH:23]=2)[CH2:20][N:19]([C:39]([C:35]2[CH:34]=[C:33]([CH3:32])[N:38]=[N:37][CH:36]=2)=[O:40])[CH2:18]1)[O:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 553007686-Methyl-4-pyridazinecarboxylic acid hydrochlorideHCID 671318282-{(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-[(3R,4S)-4-(3,4-difluoro-phenyl)-pyrrolidin-3-yl]-ethoxy}-5-chloro-pyridine

Product 1

HCID 67131615[(3R,4S)-3-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(5-chloro-pyridin-2-yloxy)-ethyl]-4-(3,4-difluoro-phenyl)-pyrrolidin-1-yl]-(6-methyl-pyridazin-4-yl)-methanone

Procedure

The titled compound was prepared following a general procedure I for amidation between 2-{(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-[(3R,4S)-4-(3,4-difluoro-phenyl)-pyrrolidin-3-yl]-ethoxy}-5-chloro-pyridine and 6-Methyl-pyridazine-4-carboxylic acid . ES-MS m/e: 589.1 (M+H+).

Sources & evidence

ORD record
ord-a113d735843947b3b37a77d07ca58f46
Source dataset
uspto-grants-2011_09
Patent number
US08012998B2

Reaction notes

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