Ammonia → HCID 86671054, compound

HRID 1037402Notes

Reaction equation

HRID 1037402 reaction equation
NC1(C2C=CC(C3C(=O)C4C(=CC=C(F)C=4)OC=3C3C=CC=CC=3)=CC=2)CCC1.C(OC(=O)[NH:36][C:37]1([C:41]2[CH:46]=[CH:45][C:44]([C:47]3[C:56](=[O:57])[C:55]4[C:50](=[C:51]([C:58]#[CH:59])[CH:52]=[CH:53][CH:54]=4)[O:49][C:48]=3[C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=3)=[CH:43][CH:42]=2)[CH2:40][CH2:39][CH2:38]1)(C)(C)C.C(O)(C(F)(F)F)=O.N>C(Cl)Cl>[NH2:36][C:37]1([C:41]2[CH:42]=[CH:43][C:44]([C:47]3[C:56](=[O:57])[C:55]4[C:50](=[C:51]([C:58]#[CH:59])[CH:52]=[CH:53][CH:54]=4)[O:49][C:48]=3[C:60]3[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=3)=[CH:45][CH:46]=2)[CH2:40][CH2:39][CH2:38]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 510305983-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-oneHCID 86671055{1-[4-(8-ethynyl-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 86671054HCID 86671054, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure of 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, {1-[4-(8-ethynyl-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester was treated with TFA. The resultant free base was subjected to flash chromatography (SiO2, gradient 0 to 20% methanolic ammonia in DCM) to afford the title compound as a white solid (8 mg, 100%). 1H NMR (400 MHz, DMSO-d6): δ 8.08 (dd, J=7.8, 1.6 Hz, 1H), 7.97 (dd, J=7.6, 1.8 Hz, 1H), 7.48 (t, J=7.4 Hz, 1H), 7.42-7.28 (m, 7H), 7.14 (d, J=8.4 Hz, 2H), 4.65 (s, 1H), 4.01 (bs, 2H), 2.42-2.33 (m, 2H), 2.17-2.07 (m, 2H), 2.03-1.91 (m, 1H), 1.71-1.58 (m, 1H). LCMS (Method E): RT=3.64 min, [M+H]+=392.

Sources & evidence

ORD record
ord-a69b59db82934b21a3858b5402fd9ea6
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

Loading…