Hydrochloric Acid → 3-[4-(1-Amino-cyclobutyl)-phenyl]-2-phenyl-chromene-4-thione hydrochloride

HRID 1037320Notes

Reaction equation

HRID 1037320 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](=[S:57])[C:55]4[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=4)[O:49][C:48]=3[C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)=[CH:43][CH:42]=2)[CH2:40][CH2:39][CH2:38]1)(C)(C)C.C(O)(C(F)(F)F)=O.[ClH:72]>CO.O>[ClH:72].[NH2:36][C:37]1([C:41]2[CH:42]=[CH:43][C:44]([C:47]3[C:56](=[S:57])[C:55]4[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=4)[O:49][C:48]=3[C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)=[CH:45][CH:46]=2)[CH2:38][CH2:39][CH2:40]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 510305983-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-oneHCID 86671045{1-[4-(2-Phenyl-4-thioxo-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 866710463-[4-(1-Amino-cyclobutyl)-phenyl]-2-phenyl-chromene-4-thione hydrochlorideYield 64%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, {1-[4-(2-phenyl-4-thioxo-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester was treated with TFA. The resultant free base was dissolved in a mixture of MeOH (2 mL), water (3 mL) and 1 M HCl (0.1 mL) and then chromatographed on a 5 g C18 cartridge {40 to 80% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)} to give the title compound as a grey-green solid (17.2 mg, 64% over 2 steps). 1H NMR (400 MHz, DMSO-d6): δ 8.63 (br s, 3H), 8.53 (dd, J=8.3 and 1.4 Hz, 1H), 7.95-7.91 (m, 1H), 7.81 (d, J=8.5 Hz, 1H), 7.61-7.57 (m, 1H), 7.48-7.39 (m, 5H), 7.34-7.26 (m, 4H), 2.57-2.49 (m, 4H), 2.23-2.13 (m, 1H), 1.85-1.74 (m, 1H). LCMS (Method E): RT=3.92 min, [M+H]+=384.

Workup

  1. customchromatographed on a 5 g C18 cartridge

Sources & evidence

ORD record
ord-2b3ed5e5aaaf493aa04be4eba156ffb2
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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