1,1-Difluoro-2-iodoethane → HCID 123893239, compound

HRID 1509223Notes

Reaction equation

C(OC(=O)NC1(C2C=CC(C3C(C4C=CC=CC=4)=CC4N(CCC#N)C(=O)COC=4N=3)=CC=2)CCC1)(C)(C)C.[O:40]=[C:41]1[CH2:46][O:45][C:44]2[N:47]=[C:48]([C:57]3[CH:62]=[CH:61][C:60]([C:63]4([NH:67][C:68](=[O:74])[O:69][C:70]([CH3:73])([CH3:72])[CH3:71])[CH2:66][CH2:65][CH2:64]4)=[CH:59][CH:58]=3)[C:49]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)=[CH:50][C:43]=2[NH:42]1.[F:75][CH:76]([F:79])[CH2:77]I>>[C:70]([O:69][C:68](=[O:74])[NH:67][C:63]1([C:60]2[CH:61]=[CH:62][C:57]([C:48]3[C:49]([C:51]4[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=4)=[CH:50][C:43]4[N:42]([CH2:77][CH:76]([F:79])[F:75])[C:41](=[O:40])[CH2:46][O:45][C:44]=4[N:47]=3)=[CH:58][CH:59]=2)[CH2:64][CH2:65][CH2:66]1)([CH3:71])([CH3:73])[CH3:72]

Participants

Reactant 3

HCID 38335651,1-Difluoro-2-iodoethane

HCID 67256382HCID 67256382, compound

HCID 123769430HCID 123769430, compound

Product 1

HCID 123893239HCID 123893239, compound

Procedure

Following the procedure for tert-butyl(1-(4-(1-(2-cyanoethyl)-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate, tert-butyl 1-(4-(2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutylcarbamate (100 mg, 0.212 mmol) was reacted with 1,1-difluoro-2-iodoethane (122 mg, 0.636 mmol) to afford the title compound (85 mg. 1H NMR (500 MHz, CDCl3): 7.42 (1H, s), 7.24-7.30 (7H, m), 7.17-7.19 (2H, m), 6.11 (1H, tt), 5.05 (1H, br), 4.92 (s, 2H), 4.28 (dt, 2H), 2.44-2.49 (m, 4H), 2.05 (m, 1H), 1.81 (m, 1H), 1.2-1.43 (br, 9H).

Sources & evidence

ORD record: ord-f7b04f751f624d58bef06c66f146cf3f
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221838B2

Reaction notes

Loading…