Ammonia → HCID 178507112, compound

HRID 1037404Notes

Reaction equation

HRID 1037404 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]5[N:59]=[N:60][NH:61][CH:62]=5)[CH:52]=[CH:53][CH:54]=4)[O:49][C:48]=3[C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=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]5[N:59]=[N:60][NH:61][CH:62]=5)[CH:52]=[CH:53][CH:54]=4)[O:49][C:48]=3[C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=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 178452580HCID 178452580, compound

Product 1

HCID 178507112HCID 178507112, compoundYield 23%

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-[4-oxo-2-phenyl-8-(1H-[1,2,3]triazol-4-yl)-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 (7 mg, 23%, 2 steps). 1H NMR (400 MHz, DMSO-d6): δ 8.40 (dd, J=7.6 and 1.8 Hz, 1H), 8.14 (s, 1H), 8.08 (dd, J=7.9 and 1.8 Hz, 1H), 7.58 (t, J=7.8 Hz, 1H), 7.48-7.44 (m, 2H), 7.41-7.31 (m, 5H), 7.11 (d, J=8.6 Hz, 2H), 3.26 (bs, 3H), 2.37-2.27 (m, 2H), 2.08-1.88 (m, 3H), 1.66-1.54 (m, 1H). LCMS (Method E): RT=2.98 min, [M+H]+=435.

Sources & evidence

ORD record
ord-ee5c72eda67a488cb381efde25650f57
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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