Methanol → HCID 50992440, compound

HRID 1037264Notes

Reaction equation

HRID 1037264 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:52](=[O:53])[C:51]4[CH:54]=[C:55]([Cl:69])[C:56]5[N:57]=[CH:58][N:59](COCC[Si](C)(C)C)[C:60]=5[C:50]=4[O:49][C:48]=3[C:70]3[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=3)=[CH:43][CH:42]=2)[CH2:40][CH2:39][CH2:38]1)(C)(C)C.C(OC(=O)NC1(C2C=CC(C3C(=O)C4C=C(Cl)C5N(CCCC[Si](C)(C)C)C=NC=5C=4OC=3C3C=CC=CC=3)=CC=2)CCC1)(C)(C)C.CO>C(Cl)Cl>[NH2:36][C:37]1([C:41]2[CH:42]=[CH:43][C:44]([C:47]3[C:52](=[O:53])[C:51]4[CH:54]=[C:55]([Cl:69])[C:56]5[N:57]=[CH:58][NH:59][C:60]=5[C:50]=4[O:49][C:48]=3[C:70]3[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=3)=[CH:45][CH:46]=2)[CH2:40][CH2:39][CH2:38]1

Participants

6

Reactant 4

HCID 887MethanolHCID 510305983-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-oneHCID 67067735HCID 67067735, compoundHCID 67067926HCID 67067926, compound

Product 1

HCID 50992440HCID 50992440, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure for 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, a mixture of (1-{4-[4-chloro-6-oxo-8-phenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1,6-dihydro-chromeno[7,8-d]imidazol-7-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester and (1-{4-[4-chloro-6-oxo-8-phenyl-3-(4-trimethylsilanyl-butyl)-3,6-dihydro-chromeno[7,8-d]imidazol-7-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester (46 mg, 0.07 mmol) were reacted to give crude product. This residue was subjected to flash chromatography [SiO2, gradient 0 to 15% MeOH (2 M NH3) in DCM] to furnish the title compound as a white solid (15 mg, 48%). LCMS (Method E): RT=2.96 min, [M+H]*=442/444. 1H NMR (400 MHz, DMSO-d6): 8.33 (s, 1H), 7.87 (s, 1H), 7.45-7.41 (m, 2H), 7.39-7.35 (m, 2H), 7.32-7.27 (m, 1H), 7.22-7.16 (m, 4H), 2.59-2.50 (m, 2H), 2.31-2.22 (m, 2H), 2.12-2.00 (m, 1H), 1.80-1.69 (m, 1H).

Workup

  1. customwere reacted
  2. customto give crude product

Sources & evidence

ORD record
ord-90ce5284398b4ae4a1299b67e7796e4b
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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