tert-Butanol → tert-butyl(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)carbamate

HRID 588144Notes

Reaction equation

C([N:3]([CH2:6]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:15])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.[CH3:59][C:60]([OH:63])([CH3:62])[CH3:61]>O>[C:60]([O:63][C:6](=[O:15])[NH:3][C:30]1[C:29]2[C:35]([O:57][CH3:58])=[N:36][N:37]([C:38]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)([C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=3)[C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C:28]=2[CH:27]=[C:26]([Cl:25])[N:31]=1)([CH3:62])([CH3:61])[CH3:59]

Participants

Conditions

Temperature: 100 °C

Procedure

Triethylamine (135 μl, 0.968 mmol) followed by diphenylphosphoryl azide (163 μl, 0.754 mmol) were added to 6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carboxylic acid (Intermediate 36B, 288 mg, 0.613 mmol) in tBuOH (6.2 ml). 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 layers 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 to give tert-butyl(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)carbamate (45B). MS: [M+H]+ m/z 541.

Workup

customRoom temperature
extractionextracted into EtOAc
washThe organic layers 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-407f44e9b5cd4b4486d740ba85d94f35
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226922B2

Reaction notes

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