Triethylamine → HCID 68586047, compound

HRID 17475Notes

Reaction equation

[CH3:1][N:2]([CH3:8])[C@H:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.C(N(CC)CC)C.F[C:17]1[C:18]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[C:19]([CH3:36])[C:20]([C:34]#[N:35])=[C:21]2[C:25]=1[O:24][C:23]([N:26]1[CH2:31][CH2:30][N:29]([CH3:32])[C:28](=[O:33])[CH2:27]1)=[N:22]2>CS(C)=O>[CH3:1][N:2]([CH3:8])[C@H:3]1[CH2:7][CH2:6][N:5]([C:17]2[C:18]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[C:19]([CH3:36])[C:20]([C:34]#[N:35])=[C:21]3[C:25]=2[O:24][C:23]([N:26]2[CH2:31][CH2:30][N:29]([CH3:32])[C:28](=[O:33])[CH2:27]2)=[N:22]3)[CH2:4]1

Participants

Conditions

Temperature: 130 °C

Procedure

(3S)-3-(Dimethylamino)pyrrolidine (67.9 μl, 0.535 mmol) and triethylamine (86.1 μl, 0.618 mmol) were added to a dimethyl sulfoxide (5 ml) solution of 7-fluoro-5-methyl-2-(4-methyl-3-oxopiperazin-1-yl)-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-188) (150 mg, 0.412 mmol), followed by stirring in an oil bath at 130° C. for 3 hours. The reaction liquid was concentrated under reduced pressure, the residue was dissolved in chloroform (50 ml), washed with saturated brine (50 ml). After drying over anhydrous sodium sulfate and concentration, the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=10:1) to obtain the entitled compound (109 mg, 54.5%) as a colorless foamy substance.

Workup

customThe reaction liquid
concentrationwas concentrated under reduced pressure
dissolutionthe residue was dissolved in chloroform (50 ml)
washwashed with saturated brine (50 ml)
dry with materialAfter drying over anhydrous sodium sulfate and concentration
customthe resulting residue was purified by preparative TLC (eluent, chloroform:methanol=10:1)

Sources & evidence

ORD record: ord-c139d2a759cd4972aa16659e114b7afb
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

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