5-Chlorothieno[3,2-b]pyridine-3-carbaldehyde → (S)-N-((5-chlorothieno[3,2-b]pyridin-3-yl)methyl)-1,1-diethoxypropan-2-amine

HRID 2274646Notes

Reaction equation

HRID 2274646 reaction equation
[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[C@@H:5]([NH2:7])[CH3:6])[CH3:2].[Cl:11][C:12]1[N:17]=[C:16]2[C:18]([CH:21]=O)=[CH:19][S:20][C:15]2=[CH:14][CH:13]=1>>[Cl:11][C:12]1[N:17]=[C:16]2[C:18]([CH2:21][NH:7][C@@H:5]([CH3:6])[CH:4]([O:8][CH2:9][CH3:10])[O:3][CH2:1][CH3:2])=[CH:19][S:20][C:15]2=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 14762645-Chlorothieno[3,2-b]pyridine-3-carbaldehydeHCID 12398111(2S)-1,1-Diethoxy-2-propanamine

Product 1

HCID 86652569(S)-N-((5-chlorothieno[3,2-b]pyridin-3-yl)methyl)-1,1-diethoxypropan-2-amineYield 30.3%

Procedure

According to the procedure described in the synthesis method of Compound IX-6, (S)-1,1-diethoxypropan-2-amine (Compound XVIII-1) (1.98 g, 13.4 mmol) was reacted with 5-chlorothieno[3,2-b]pyridine-3-carbaldehyde (Compound XIX-1) (1.98 g, 10 mmol) and the obtained residue was purified by Büch silica gel column chromatography (eluent: chloroform:methanol=98:2 to 95:5) to obtain the title compound (996 mg, 30%).

Workup

  1. customthe obtained residue was purified by Büch silica gel column chromatography (eluent: chloroform:methanol=98:2 to 95:5)

Sources & evidence

ORD record
ord-dd963f99803f4e94aa3379ce37002487
Source dataset
uspto-grants-2015_09
Patent number
US09126981B2

Reaction notes

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