Azide → HCID 86613762, compound

HRID 1172562Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[CH2:14][C@H:15]([CH2:18]O)[CH2:16][CH2:17][C@@H:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].S([O-])(=O)(=O)C.[N-]=[N+:26]=[N-:27].[O:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[C:33]1[N:46]=[C:36]2[N:37]=[C:38](S(C)(=O)=O)[N:39]=[C:40]([NH2:41])[N:35]2N=1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[CH2:14][C@H:15]([CH2:18][NH:41][C:40]3[N:39]=[C:38]([NH2:37])[N:27]4[N:26]=[C:33]([C:29]5[O:28][CH:32]=[CH:31][CH:30]=5)[N:46]=[C:36]4[N:35]=3)[CH2:16][CH2:17][C@@H:10]2[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Reactant 4

HCID 33558Azide

HCID 85257Methanesulfonate

HCID 99708822-(Furan-2-yl)-5-(methylsulfonyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-amine

HCID 22940599HCID 22940599, compound

Product 1

HCID 86613762HCID 86613762, compound

Procedure

7-Hydroxymethyl-octahydro-pyrido[1,2-a]pyrazine-2-carboxylic acid tert-butyl ester (see subpart (a) above), was converted to the corresponding mesylate, azide and amine sequentially according to Example 6, subparts (b)-(d) above. The corresponding amine was coupled to 2-furan-2-yl-5-methanesulfonyl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine in accordance to Example 1 to afford trans-7-[(7-amino-2-furan-2-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-ylamino)-methyl]-octahydro-pyrido[1,2-a]pyrazine-2-carboxylic acid tert-butyl ester as yellow oil. This material was used in the next step without further purification.

Sources & evidence

ORD record: ord-198f7aba61684a6bb033053e1fa1e861
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834014B2

Reaction notes

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