N-Cbz-d-alanine → Phenylmethyl{(1R)-1-[6-bromo-3-({[2-(trimethylsilyl)ethyl]oxy}methyl)-3H-imidazo[4,5-b]pyridin-2-yl]ethyl}({[2-(trimethylsilyl)ethyl]oxy}methyl)carbamate

HRID 241028

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[N:6][CH:7]=1.[CH2:10]([O:17][C:18]([NH:20][C@@H:21]([C:23](O)=O)[CH3:22])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH3:26][Si:27]([CH3:34])([CH3:33])[CH2:28][CH2:29][O:30][CH2:31]Cl>>[C:11]1([CH2:10][O:17][C:18](=[O:19])[N:20]([C@@H:21]([C:22]2[N:8]([CH2:31][O:30][CH2:29][CH2:28][Si:27]([CH3:34])([CH3:33])[CH3:26])[C:5]3=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=[C:4]3[N:9]=2)[CH3:23])[CH2:31][O:30][CH2:29][CH2:28][Si:27]([CH3:34])([CH3:33])[CH3:26])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

Reactant 3

HCID 70832N-Cbz-d-alanine

HCID 6911565-Bromopyridine-2,3-diamine

HCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 68773284Phenylmethyl{(1R)-1-[6-bromo-3-({[2-(trimethylsilyl)ethyl]oxy}methyl)-3H-imidazo[4,5-b]pyridin-2-yl]ethyl}({[2-(trimethylsilyl)ethyl]oxy}methyl)carbamate

Procedure

Synthesized according to the method of reagent preparation 19 by using 5-bromo-2,3-diaminopyridine and N-(benzyloxycarbonyl)-D-alanine in step 1 and 2-(trimethylsilyl)ethoxymethyl chloride in step 3. MS (EI) for C28H43BrN34O4Si2: 636 (MH+).

Workup

customSynthesized
customaccording to the method of reagent preparation 19

Sources & evidence

ORD record: ord-051b6384e3ef49d690af3c5d455552cf
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648066B2

Linked notes

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