Triethylamine → 6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-amine

HRID 588146Notes

Reaction equation

C([N:3](CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[Cl:25][C:26]1[N:31]=[C:30](C(O)=O)[C:29]2[C:35]([O:57][CH3:58])=[N:36][N:37]([C:38]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:28]=2[CH:27]=1>O1CCOCC1.O>[Cl:25][C:26]1[N:31]=[C:30]([NH2:3])[C:29]2[C:35]([O:57][CH3:58])=[N:36][N:37]([C:38]([C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=3)([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[C:28]=2[CH:27]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Triethylamine (370 μl, 2.66 mmol) followed by diphenylphosphoryl azide (447 μl, 2.068 mmol) were added to 6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carboxylic acid (36B, 790 mg, 1.681 mmol) in 1,4-dioxane (16.5 ml) a 100 ml roundbottom flask attached to a reflux condenser. The mixture was allowed to stir at 100° C. overnight. Room temperature was attained and the reaction mixture was diluted with water and extracted into EtOAc. The organic layer was washed with NaHCO3, brine, dried over NaSO4, and concentrated in vacuo. The material was loaded onto silica gel and purified by MPLC 0-25% EtOAc/hexanes gave 6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-amine MS: [M+H]+ m/z 441.

Workup

customattached to a reflux condenser
customRoom temperature
extractionextracted into EtOAc
washThe organic layer was washed with NaHCO3, brine
dry with materialdried over NaSO4
concentrationconcentrated in vacuo
custompurified by MPLC 0-25% EtOAc/hexanes

Sources & evidence

ORD record: ord-dc33f31481cf47d7a92372d0a24733cb
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226922B2

Reaction notes

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