(R)-O-((2,2-Dimethyl-1,3-dioxolan-4-yl)methyl)hydroxylamine → (R)-5-(4-Bromo-2-fluorophenylamino)-N-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)imidazo[1,5-a]pyrazine-6-carboxamide

HRID 2064044Notes

Reaction equation

HRID 2064044 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]3[CH:15]=[N:16][CH:17]=[C:13]3[CH:12]=[N:11][C:10]=2[C:18](NOCCOC=C)=[O:19])=[C:4]([F:27])[CH:3]=1.[CH3:28][C:29]1([CH3:37])[O:33][C@@H:32]([CH2:34][O:35][NH2:36])[CH2:31][O:30]1>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]3[CH:15]=[N:16][CH:17]=[C:13]3[CH:12]=[N:11][C:10]=2[C:18]([NH:36][O:35][CH2:34][C@H:32]2[CH2:31][O:30][C:29]([CH3:37])([CH3:28])[O:33]2)=[O:19])=[C:4]([F:27])[CH:3]=1

Participants

3

Reactant 2

HCID 11298047(R)-O-((2,2-Dimethyl-1,3-dioxolan-4-yl)methyl)hydroxylamineHCID 591401825-(4-Bromo-2-fluorophenylamino)-N-(2-(vinyloxy)ethoxy)-imidazo[1,5-a]pyrazine-6-carboxamide

Product 1

HCID 59140128(R)-5-(4-Bromo-2-fluorophenylamino)-N-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)imidazo[1,5-a]pyrazine-6-carboxamide

Procedure

The desired compound was prepared in an analogous fashion to 5-(4-bromo-2-fluorophenylamino)-N-(2-(vinyloxy)ethoxy)-imidazo[1,5-a]pyrazine-6-carboxamide, using (R)—O-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)hydroxylamine as the starting material. LCMS (method D1): RT=0.954 min, [M+H]+=480/482.

Sources & evidence

ORD record
ord-5bb856fecacd49118be47d1acb285cda
Source dataset
uspto-grants-2012_10
Patent number
US08288408B2

Reaction notes

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