Bicarbonate Ion → HCID 90413553, compound

HRID 1526659Notes

Reaction equation

HRID 1526659 reaction equation
[NH2:1][C:2]1[O:3][C@H:4]2[C@@H:6]([C@:7]([C:12]3[CH:13]=[C:14]([NH:19][C:20](=[O:30])[C:21]4[C:26]([CH2:27]O)=[CH:25][C:24]([Cl:29])=[CH:23][N:22]=4)[CH:15]=[CH:16][C:17]=3[F:18])([CH:9]([F:11])[F:10])[N:8]=1)[CH2:5]2.COCCN(S(F)(F)F)CCOC.C(=O)(O)[O-]>C(Cl)Cl.C1COCC1>[NH2:1][C:2]1[O:3][C@H:4]2[C@@H:6]([C@:7]([C:12]3[CH:13]=[C:14]([N:19]4[CH2:27][C:26]5[C:21](=[N:22][CH:23]=[C:24]([Cl:29])[CH:25]=5)[C:20]4=[O:30])[CH:15]=[CH:16][C:17]=3[F:18])([CH:9]([F:11])[F:10])[N:8]=1)[CH2:5]2

Participants

6

Reactant 3

HCID 769Bicarbonate IonHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 90413325HCID 90413325, compound

Product 1

HCID 90413553HCID 90413553, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-(3-((1R,5S,6R)-3-amino-5-(difluoromethyl)-2-oxa-4-azabicyclo[4.1.0]hept-3-en-5-yl)-4-fluorophenyl)-5-chloro-3-(hydroxymethyl)picolinamide (Example 420, 60 mg, 0.136 mmol) in DCM (2 mL) was cooled 0° C. under nitrogen atmosphere. A solution of Deoxo-fluor, (50 w % in THF, 0.150 mL, 0.408 mmol) was added dropwise and the reaction mixture was allowed to stir at rt for 25 min. The reaction mixture was poured into aqueous saturated bicarbonate solution and extracted with EtOAc. The crude material was absorbed onto a plug of silica gel and purified by chromatography, eluting with a gradient of 20% to 100% EtOAc in hexane, to provide the title compound as white solid. MS m/z=423 [M+H]+.

Workup

  1. extractionextracted with EtOAc
  2. customThe crude material was absorbed onto a plug of silica gel
  3. custompurified by chromatography
  4. washeluting with a gradient of 20% to 100% EtOAc in hexane

Sources & evidence

ORD record
ord-5117ae482bde42ffa00ce19dfe5ddbb6
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

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