(Diethylamino)sulfur trifluoride → HCID 67228960, compound

HRID 2067860Notes

Reaction equation

HRID 2067860 reaction equation
FC(F)(F)C([N:5]([C@@H:14]1[CH2:18][CH2:17][C@@:16]([C:22]([N:24]2[CH2:29][C@@H:28]3[C@H:30](O)[C@H:25]2[CH2:26][N:27]3[C:32]2[CH:37]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:35]=[CH:34][N:33]=2)=[O:23])([CH:19]([CH3:21])[CH3:20])[CH2:15]1)[C@H:6]1[CH2:11][CH2:10][O:9][CH2:8][C@H:7]1[O:12][CH3:13])=O.CCN(S(F)(F)[F:50])CC>C(Cl)Cl>[F:50][CH:30]1[C@@H:28]2[N:27]([C:32]3[CH:37]=[C:36]([C:38]([F:41])([F:39])[F:40])[CH:35]=[CH:34][N:33]=3)[CH2:26][C@H:25]1[N:24]([C:22]([C@@:16]1([CH:19]([CH3:20])[CH3:21])[CH2:17][CH2:18][C@@H:14]([NH:5][C@H:6]3[CH2:11][CH2:10][O:9][CH2:8][C@H:7]3[O:12][CH3:13])[CH2:15]1)=[O:23])[CH2:29]2

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 86654425HCID 86654425, compound

Product 1

HCID 67228960HCID 67228960, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,2,2-trifluoro-N-((1R,3S)-3-((1R,4R,7S)-7-hydroxyl-2-(4-(trifluoromethyl)pyridin-2-yl)-2,5-diaza-bicyclo[2.2.1]heptane-5-carbonyl)-3-isopropylcyclopentyl)-N-((3S,4S)-3-methoxy-tetrahydro-2H-pyran-4-yl)acetamide (30 mg, 0.057 mmol) in CH2Cl2 (2 ml) was cooled to 0° C. and DAST (0.025 ml, 0.086 mmol) was added to the solution. The reaction mixture was stirred overnight and purified by chromatography (10% EtOAc to 100% MeOH) to yield desired product (16 mg, 32%). LC/MS (M+H)=529.2802 exp, 529.3112 obs; 1H NMR (400 MHz, DMSO-d6) δ ppm 0.67-0.78 (m, 5H) 0.82 (d, J=6.59 Hz, 3H) 1.23 (br. s., 1H) 1.50 (d, J=3.66 Hz, 3H) 1.75 (d, J=4.39 Hz, 2H) 1.94-2.03 (m, 1H) 2.24-2.32 (m, 1H) 2.98 (s, 1H) 3.12 (br. s., 1H) 3.18-3.23 (m, 4H) 3.31-3.34 (m, 1H) 3.40 (d, J=10.98 Hz, 1H) 3.62 (d, J=12.08 Hz, 1H) 3.72 (d, J=10.62 Hz, 3H) 3.80-3.92 (m, 1H) 4.87 (br. s., 1H) 4.90-4.96 (m, 1H) 5.31 (d, J=1.83 Hz, 1H) 5.40-5.46 (m, 1H) 6.86-6.94 (m, 2H) 8.31 (d, J=5.49 Hz, 1H)

Workup

  1. custompurified by chromatography (10% EtOAc to 100% MeOH)

Sources & evidence

ORD record
ord-4aa84e4ac824410d9e6a1316f760e21a
Source dataset
uspto-grants-2012_10
Patent number
US08293903B2

Reaction notes

Loading…