Acetaldehyde → HCID 57831007, compound

HRID 1642078Notes

Reaction equation

C(=O)C.C(N[C:8]([C:10]1[N:11]=[C:12]2[C:18]([C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:17][NH:16][C:13]2=[N:14][CH:15]=1)=[O:9])(C)C.[CH:25](N)([CH3:27])[CH3:26].C(C1N=C2C(C(=O)C(C)(C)C)=CNC2=NC=1)(=O)C.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>>[OH:9][CH:8]([C:10]1[N:11]=[C:12]2[C:18]([C:19](=[O:24])[C:20]([CH3:21])([CH3:22])[CH3:23])=[CH:17][NH:16][C:13]2=[N:14][CH:15]=1)[CH:25]([CH3:27])[CH3:26]

Participants

Reactant 5

HCID 177Acetaldehyde2×

HCID 6363Isopropylamine

HCID 159087Triacetoxyperiodinane

HCID 44200068HCID 44200068, compound

HCID 44200069HCID 44200069, compound

Product 1

HCID 57831007HCID 57831007, compound

Procedure

Substituting isobutyraldehyde for acetaldehyde in Step 2. MP=148-150 C, (M+H)+=276. 7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazine-2-carboxylic acid isopropylamide Substituting carbon dioxide for acetaldehyde in Step 2. Then following general procedures described in these Examples, using isopropylamine and continuing with Step 3. MP=206-208 C, (M+H)+=289. 1-(2-Acetyl-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethyl-propan-1-one. The product of Step 3 was treated with Dess-Martin periodinane, following general procedures described in these Examples. MP=221-223 C, (M+H)+=246.

Sources & evidence

ORD record: ord-fd1d199cd8b544a0a06fa89d3f938b6a
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119636B2

Reaction notes

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