Hydrochloric Acid → 5-[4-(2-Azepin-1-yl-ethoxy)-phenoxy]-6-(4-methanesulfonyl-phenyl)-naphthalen-2-ol Hydrochloride

HRID 748924Notes

Reaction equation

HRID 748924 reaction equation
[ClH:1].[CH3:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:22]C)[CH:18]=3)[C:13]=2[O:24][C:25]2[CH:40]=[CH:39][C:28]([O:29][CH2:30][CH2:31][N:32]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=[CH:33]3)=[CH:27][CH:26]=2)=[CH:8][CH:7]=1)(=[O:5])=[O:4].N1(CCOC2C=CC(OC3C(C4C=CC(S(C)(=O)=O)=CC=4)=CC=C4C=3C=CC(O)=C4)=CC=2)C=CC=CC=C1.Cl>ClCCl.CCOCC>[ClH:1].[N:32]1([CH2:31][CH2:30][O:29][C:28]2[CH:27]=[CH:26][C:25]([O:24][C:13]3[C:12]([C:9]4[CH:10]=[CH:11][C:6]([S:3]([CH3:2])(=[O:4])=[O:5])=[CH:7][CH:8]=4)=[CH:21][CH:20]=[C:19]4[C:14]=3[CH:15]=[CH:16][C:17]([OH:22])=[CH:18]4)=[CH:40][CH:39]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=[CH:33]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 685159301-(2-{4-[2-(4-Methanesulfonyl-phenyl)-6-methoxy-naphthalen-1-yloxy]-phenoxy}-ethyl)-azepine HydrochlorideHCID 685204515-[4-(2-Azepin-1-yl-ethoxy)-phenoxy]-6-(4-methanesulfonyl-phenyl)-naphthalen-2-ol

Product 1

HCID 685204505-[4-(2-Azepin-1-yl-ethoxy)-phenoxy]-6-(4-methanesulfonyl-phenyl)-naphthalen-2-ol HydrochlorideYield 92.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Convert the compound of Example 60 (160 mg, 0.27 mmol) to 5-[4-(2-azepin-1-yl-ethoxy)-phenoxy]-6-(4-methanesulfonyl-phenyl)-naphthalen-2-ol using a procedure similar to Preparation 15 (85%). Dissolve the free base in dichloromethane, add 1N HCl in Et2O (0.250 mL) then concentrate to give 140 mg of the title compound. Mass spectrum (ion spray): m/z=532 (M+H).

Workup

  1. concentrationthen concentrate

Sources & evidence

ORD record
ord-bf76665e6b874bb68fb8a697cbb560fd
Source dataset
uspto-grants-2008_07
Patent number
US07399867B2

Reaction notes

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