(Diethylamino)sulfur trifluoride → HCID 59427365, compound

HRID 1013776Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([O:13][C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21]4[C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[C:24]([C:31]5[S:35][CH:34]=[C:33]([CH2:36]O)[CH:32]=5)=[N:23][N:22]=4)=[CH:16][CH:15]=3)=[CH:8][CH:9]=[N:10]2)=[N:5][CH:4]=1.C(N(S(F)(F)[F:44])CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:44][CH2:36][C:33]1[CH:32]=[C:31]([C:24]2[C:25]3[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:21]([NH:20][C:17]3[CH:18]=[CH:19][C:14]([O:13][C:7]4[C:6]5[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][N:5]=5)[N:10]=[CH:9][CH:8]=4)=[CH:15][CH:16]=3)=[N:22][N:23]=2)[S:35][CH:34]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A round bottom flask was charged with (5-(4-(4-(7-methoxy-1,5-naphthyridin-4-yloxy)phenylamino)phthalazin-1-yl)thiophen-3-yl)methanol (71 mg, 140 μmol) and 2.8 mL DCM, and the mixture was cooled to 0° C. under nitrogen. (Diethylamino) trifluorosulfur (55 μl, 420 μmol) was added, and the mixture was stirred at 0° C. for 20 min and was then allowed to warm to RT. After another 0.5 h, saturated NaHCO3 was added and the mixture was stirred for 10 min. The solids were filtered, and the crude material was purified by silica gel chromatography, 90/10/1 DCM/MeOH/NH4OH in DCM, followed by reverse phase chromatography, Gilson, 10-90% 0.1% TFA/ACN in water, to provide the titled compound. MS: [M+H]=510.

Workup

temperatureto warm to RT
waitAfter another 0.5 h
stirringthe mixture was stirred for 10 min
filtrationThe solids were filtered
customthe crude material was purified by silica gel chromatography, 90/10/1 DCM/MeOH/NH4OH in DCM

Sources & evidence

ORD record: ord-5463051436d841e690de4b23fca34981
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981891B2

Reaction notes

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