Pramipexole → (-)-N6-(2-(4-(8-((4-Methoxybenzyl)oxy)quinoline-4-yl)piperazine-1-yl)ethyl)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine

HRID 574292

Reaction equation

[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:18]=2[N:17]=[CH:16][CH:15]=[C:14]3[N:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH:26]=O)[CH2:21][CH2:20]2)=[CH:5][CH:4]=1.[CH3:30][CH2:31][CH2:32][NH:33][C@@H:34]1[CH2:39][C:38]2[S:40][C:41]([NH2:43])=[N:42][C:37]=2[CH2:36][CH2:35]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:18]=2[N:17]=[CH:16][CH:15]=[C:14]3[N:19]2[CH2:20][CH2:21][N:22]([CH2:25][CH2:26][N:33]([CH2:32][CH2:31][CH3:30])[CH:34]3[CH2:35][CH2:36][C:37]4[N:42]=[C:41]([NH2:43])[S:40][C:38]=4[CH2:39]3)[CH2:23][CH2:24]2)=[CH:5][CH:4]=1

Participants

Reactant 3

HCID 119570Pramipexole

HCID 5049666Sodium triacetoxyborohydride

HCID 866646662-(4-(8-((4-Methoxybenzyl)oxy)quinoline-4yl)piperazine-1yl)acetaldehyde

Product 1

HCID 87424865(-)-N6-(2-(4-(8-((4-Methoxybenzyl)oxy)quinoline-4-yl)piperazine-1-yl)ethyl)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamineYield 75%

Procedure

Compound 27 (1.0 g, 2.55 mmol) was treated with (−)-pramipexole (599 mg, 2.81 mmol) and NaBH(OAc)3 (973 mg, 4.59 mmol) by following procedure A. The reaction mixture was purified by silica gel column chromatography (EtOAc/MeOH, 9:1) to yield 1.12 g (75%) of compound (−)-28 as yellow solid. The 1H NMR of (−)-28 is similar to compound (±)-28.

Workup

customThe reaction mixture was purified by silica gel column chromatography (EtOAc/MeOH, 9:1)

Sources & evidence

ORD record: ord-ba998cb8b228427cb0ea7cd2157fac5d
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034877B2

Linked notes

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