1,4-Dioxane hydrochloride → 6-[(3R)-3-Aminopiperidin-1-yl]-5-(2-chlorobenzyl)-2-(3-ethoxyphenoxy)-3-methyl-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidine-7-carbonitrile hydrochloride

HRID 1819291Notes

Reaction equation

Cl.O1CCOCC1.[Cl:8][C:9]1[CH:52]=[CH:51][CH:50]=[CH:49][C:10]=1[CH2:11][N:12]1[C:20]2[C:19](=[O:21])[N:18]([CH3:22])[C:17]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH2:31][CH3:32])[CH:25]=3)=[N:16][C:15]=2[C:14]([C:33]#[N:34])=[C:13]1[N:35]1[CH2:40][CH2:39][CH2:38][C@@H:37]([NH:41]C(=O)OC(C)(C)C)[CH2:36]1>O1CCOCC1>[ClH:8].[NH2:41][C@@H:37]1[CH2:38][CH2:39][CH2:40][N:35]([C:13]2[N:12]([CH2:11][C:10]3[CH:49]=[CH:50][CH:51]=[CH:52][C:9]=3[Cl:8])[C:20]3[C:19](=[O:21])[N:18]([CH3:22])[C:17]([O:23][C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH2:31][CH3:32])[CH:25]=4)=[N:16][C:15]=3[C:14]=2[C:33]#[N:34])[CH2:36]1

Participants

Conditions

Temperature: 25 °C

Procedure

A 4N hydrochloric acid/1,4-dioxane solution (5 ml) was added to a solution of tert-butyl {(3R)-1-[5-(2-chlorobenzyl)-7-cyano-2-(3-ethoxyphenoxy)-3-methyl-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidine-3-yl}carbamate (185 mg) in 1,4-dioxane (3 ml), and the resulting mixture was stirred at 25° C. for 2 hours and then concentrated under reduced pressure to obtain the title compound (170 mg).

Workup

concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-344a19921e3b444aabc19c618db751f7
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601728B2

Reaction notes

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