(Diethylamino)sulfur trifluoride → HCID 131732947, compound

HRID 2171607Notes

Reaction equation

HRID 2171607 reaction equation
[Si:1]([O:8][C@@H:9]1[C@@H:16]2[N:12]([N:13]=[C:14]([C:21]3[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([Cl:29])[C:22]=3[CH3:30])[C@H:15]2[O:17][CH2:18][CH2:19]O)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CCN(S(F)(F)[F:37])CC>C(Cl)Cl>[Si:1]([O:8][C@@H:9]1[C@@H:16]2[N:12]([N:13]=[C:14]([C:21]3[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([Cl:29])[C:22]=3[CH3:30])[C@H:15]2[O:17][CH2:18][CH2:19][F:37])[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 71241133HCID 71241133, compound

Product 1

HCID 131732947HCID 131732947, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 4-((3S,3aR,4S)-4-((tert-butyldimethylsilyl)oxy)-3-(2-hydroxyethoxy)-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-2-chloro-3-methylbenzonitrile (30 mg, 0.066 mmol) in DCM (3 mL) at 0° C. was added DAST (0.008 mL, 0.066 mmol) and stirred for 1 h. Once the starting material had disappeared (monitored by TLC), reaction mixture was diluted with DCM and washed with water, brine, dried over Na2SO4 and concentrated to get the crude product which was used in the next step without any purification.

Workup

  1. custom(monitored by TLC), reaction mixture
  2. washwashed with water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b044d579eee0413fb9a5fbd1bb11b712
Source dataset
uspto-grants-2015_06
Patent number
US09051326B2

Reaction notes

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