Hydrochloric Acid → HCID 67067918, compound

HRID 1037284Notes

Reaction equation

HRID 1037284 reaction equation
NC1(C2C=CC(C3C(=O)C4C(=C(C5CC5)C=CC=4)OC=3C3C=CC=CC=3)=CC=2)CCC1.[NH2:32][C:33]1([C:37]2[CH:42]=[CH:41][C:40]([C:43]3[C:52](=[O:53])[C:51]4[C:46](=[C:47]([C:54]5[CH:55]=[N:56][N:57]([CH3:59])[CH:58]=5)[CH:48]=[CH:49][CH:50]=4)[O:45][C:44]=3[C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=3)=[CH:39][CH:38]=2)[CH2:36][CH2:35][CH2:34]1.[ClH:66]>CO.O>[ClH:66].[NH2:32][C:33]1([C:37]2[CH:38]=[CH:39][C:40]([C:43]3[C:52](=[O:53])[C:51]4[C:46](=[C:47]([C:54]5[CH:55]=[N:56][N:57]([CH3:59])[CH:58]=5)[CH:48]=[CH:49][CH:50]=4)[O:45][C:44]=3[C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=3)=[CH:41][CH:42]=2)[CH2:34][CH2:35][CH2:36]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 51029865HCID 51029865, compound2×HCID 51029866HCID 51029866, compound

Product 1

HCID 67067918HCID 67067918, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-8-cyclopropyl-2-phenyl-chromen-4-one, a mixture containing 30% 3-[4-(1-amino-cyclobutyl)-phenyl]-8-(1-methyl-1H-pyrazol-4-yl)-2-phenyl-chromen-4-one and 70% 3-[4-(1-amino-cyclobutyl)-phenyl]-8-cyclopropyl-2-phenyl-chromen-4-one was dissolved in a mixture of MeOH (7 mL), water (7 mL) and 1 M HCl (0.6 mL) and chromatographed on a 5 g C18 cartridge {gradient 10 to 90% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)} to give the title compound as a white solid (5 mg). 1H NMR (300 MHz, DMSO-d6): δ 8.77 (s, 3H), 8.23 (s, 1H), 8.09 (dd, J=7.9 and 2.0 Hz, 1H), 8.02-7.97 (m, 2H), 7.70-7.34 (m, 8H), 7.29 (d, J=8.7 Hz, 2H), 3.88 (s, 3H), 2.62-2.48 (m, 4H), 2.29-2.11 (m, 1H), 1.88-1.71 (m, 1H). LCMS (Method E): RT=3.34 min, [M+H]+=448, and 3-[4-(1-amino-cyclobutyl)-phenyl]-8-cyclopropyl-2-phenyl-chromen-4-one hydrochloride.

Workup

  1. customchromatographed on a 5 g C18 cartridge {gradient 10 to 90% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)}

Sources & evidence

ORD record
ord-174a15add8e34687a745de413347e9d4
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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