Bromomethylcyclopropane → HCID 86608844, compound

HRID 1162718Notes

Reaction equation

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

Participants

Reactant 2

HCID 81503Bromomethylcyclopropane

HCID 86608842HCID 86608842, compound

Product 1

HCID 86608844HCID 86608844, compound

Procedure

In analogy to example 94.3 5-chloro-thiophene-2-carboxylic acid {(3S,4S)-4-methoxy-1-[(4,5,6,7-tetrahydro-thiazolo[5,4]pyridin-2-ylcarbamoyl)-methyl]-pyrrolidin-3-yl}-amide dihydrochloride (example 94.2) was reacted with 1-(bromomethyl)cyclopropane to give 5-chloro-thiophene-2-carboxylic acid {(3S,4S)-1-[(5-cyclopropylmethyl-4,5,6,7-tetrahydro-thiazolo[5,4]pyridin-2-ylcarbamoyl)-methyl]-4-methoxy-pyrrolidin-3-yl}-amide. Yellow solid. MS 510.5 ([M+H]+)

Sources & evidence

ORD record: ord-7f1eb0471b174db8a642c34c5cf06565
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820699B2

Reaction notes

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