(Diethylamino)sulfur trifluoride → HCID 67112685, compound

HRID 1177423Notes

Reaction equation

HRID 1177423 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:26][N:27]2[CH2:30][C:29](O)([C:31]([O:33][CH3:34])=[O:32])[CH2:28]2)[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18]1)[N:11]=2.CCN(S(F)(F)[F:42])CC>C(Cl)Cl>[F:42][C:29]1([C:31]([O:33][CH3:34])=[O:32])[CH2:28][N:27]([CH2:26][C:4]2[CH:5]=[CH:6][C:7]([C:8]3[S:9][C:10]4[C:15]([N:16]=3)=[CH:14][CH:13]=[C:12]([C:17]3([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[CH2:19][CH2:18]3)[N:11]=4)=[C:2]([F:1])[CH:3]=2)[CH2:30]1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 67111706HCID 67111706, compound

Product 1

HCID 67112685HCID 67112685, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 1-((3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)-3-hydroxyazetidine-3-carboxylate (0.0334 g, 0.068 mmol) at 0° C. in anhydrous DCM was added 1.0 mL was added DAST (0.011 mL, 0.082 mmol). The reaction mixture was stirred for 10 min. at which time the reaction was quenched carefully with water and extracted with DCM. The organics were dried over magnesium sulfate and concentrate in vacuo. Purification by silica gel afford methyl 3-fluoro-1-((3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)azetidine-3-carboxylate. MS (ESI) m/z: Calculated 491.2; Observed: 492.0 (M++1).

Workup

  1. customwas quenched carefully with water
  2. extractionextracted with DCM
  3. dry with materialThe organics were dried over magnesium sulfate
  4. concentrationconcentrate in vacuo
  5. customPurification by silica gel

Sources & evidence

ORD record
ord-8b0189edab184f1899e432f22a42e7af
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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