Difluoroacetic acid → HCID 67438657, compound

HRID 404512Notes

Reaction equation

[F:1][CH:2]([F:6])[C:3](O)=[O:4].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[O:40]1[CH2:45][CH2:44][N:43]([C:46]2[N:51]=[C:50]([N:52]3[CH2:57][CH2:56][O:55][CH2:54][CH2:53]3)[N:49]=[C:48]([C:58]3[CH:64]=[CH:63][C:61]([NH2:62])=[CH:60][CH:59]=3)[N:47]=2)[CH2:42][CH2:41]1>CN(C=O)C>[N:43]1([C:46]2[N:51]=[C:50]([N:52]3[CH2:57][CH2:56][O:55][CH2:54][CH2:53]3)[N:49]=[C:48]([C:58]3[CH:64]=[CH:63][C:61]([NH:62][C:3](=[O:4])[CH:2]([F:6])[F:1])=[CH:60][CH:59]=3)[N:47]=2)[CH2:42][CH2:41][O:40][CH2:45][CH2:44]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 2,2-difluoroacetic acid (20 mg, 0.21 mmol), HBTU (76 mg, 0.2 mmol), and DIEA (52 mg, 0.40 mmol) in 2 mL of DMF was added 4-(4,6-dimorpholino-1,3,5-triazin-2-yl) aniline (40 mg, 0.12 mmol). The reaction was stirred at 60° C. 16 hr. Then the reaction mixture was cooled to room temperature and purified by reverse phase chromatography to give N-[4-(4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl)phenyl]-2,2-difluoroacetamide (23 mg, 46% yield). HPLC: Rt=2.19 min; MS 421 [M+H].

Workup

custom16 hr
temperatureThen the reaction mixture was cooled to room temperature
custompurified by reverse phase chromatography

Sources & evidence

ORD record: ord-bd6fd0bd38784d38a5a01be8ee3a5224
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748421B2

Reaction notes

Loading…