3-((Tert-butyldimethylsilyl)oxy)propanal → HCID 67324924, compound

HRID 1401766Notes

Reaction equation

HRID 1401766 reaction equation
Cl.[CH3:2][C:3]1([CH3:24])[C:11]2[C:6](=[CH:7][C:8]([C:12]3[N:13]=[C:14]([N:17]4[CH2:22][CH2:21][CH:20]([NH2:23])[CH2:19][CH2:18]4)[S:15][CH:16]=3)=[CH:9][CH:10]=2)[CH2:5][CH2:4]1.[Si]([O:32][CH2:33][CH2:34][CH:35]=O)(C(C)(C)C)(C)C.C[N+](C)(C)C.C1COCC1>>[CH3:2][C:3]1([CH3:24])[C:11]2[C:6](=[CH:7][C:8]([C:12]3[N:13]=[C:14]([N:17]4[CH2:22][CH2:21][CH:20]([NH:23][CH2:35][CH2:34][CH2:33][OH:32])[CH2:19][CH2:18]4)[S:15][CH:16]=3)=[CH:9][CH:10]=2)[CH2:5][CH2:4]1

Participants

4

Reactant 3

HCID 36623923-((Tert-butyldimethylsilyl)oxy)propanalHCID 67323525HCID 67323525, compoundHCID 86671824HCID 86671824, compound

Product 1

HCID 67324924HCID 67324924, compound

Procedure

The preparation is carried out starting from 1-[4-(1,1-dimethylindan-5-yl)thiazol-2-yl]piperidin-4-ylamine hydrochloride and 3-(tert-butyldimethylsilanyloxy)propionaldehyde. The protecting group is cleaved off by means of a 1M tetramethylammonium/THF solution: The reaction mixture was stirred at room temperature overnight and subsequently evaporated to dryness. The product was purified by means of preparative HPLC and converted into the hydrochloride by treatment with methanolic HCl.

Workup

  1. customsubsequently evaporated to dryness
  2. customThe product was purified by means of preparative HPLC

Sources & evidence

ORD record
ord-321cb60dbcd2441590502c6a9e879676
Source dataset
uspto-grants-2014_12
Patent number
US08907098B2

Reaction notes

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