4-Chlorophenol → HCID 131732587, compound

HRID 876361Notes

Reaction equation

HRID 876361 reaction equation
[CH3:1][N:2]1[CH2:8][CH2:7][CH:6]([OH:9])[C:5]2[CH:10]=[CH:11][C:12]([C:14]3[N:15]=[N:16][CH:17]=[CH:18][CH:19]=3)=[CH:13][C:4]=2[CH2:3]1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24](O)=[CH:23][CH:22]=1.[C:28]([CH:31]([CH:33]([C:35]([OH:37])=[O:36])[OH:34])[OH:32])([OH:30])=[O:29].ClC1C=CC(C2CCNCC3C=C(C4N=NC=CC=4)C=CC2=3)=CC=1>>[C:28]([CH:31]([CH:33]([C:35]([OH:37])=[O:36])[OH:34])[OH:32])([OH:30])=[O:29].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([O:9][CH:6]2[CH2:7][CH2:8][N:2]([CH3:1])[CH2:3][C:4]3[CH:13]=[C:12]([C:14]4[N:15]=[N:16][CH:17]=[CH:18][CH:19]=4)[CH:11]=[CH:10][C:5]2=3)=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 46844-ChlorophenolHCID 68502906HCID 68502906, compoundHCID 131732588HCID 131732588, compound

Product 1

HCID 131732587HCID 131732587, compound

Procedure

This compound was prepared from (−)-2-methyl-8-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-5-ol from Step H in Example 1 and 4-chlorophenol, following the procedures of Steps J and K in Example 1. (+)-5-(4-Chlorophenyl)-8-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[c]azepine, tartrate salt (AUC HPLC>99%) is a white solid: mp 106-108° C.; 1H NMR (CD3OD, 500 MHz) δ 9.18 (d, J=5.0 Hz, 1H), 8.20-8.17 (m, 2H), 8.07 (d, J=8.0 Hz, 1H), 7.80 (dd, J=8.7, 3.8 Hz, 1H), 7.66 (d, J=7.9 Hz, 1H), 7.25 (d, J=9.0 Hz, 2H), 7.05 (d, J=9.0 Hz, 2H), 5.73 (d, J=7.6 Hz, 1H), 4.92-4.84 (m, 1H), 4.52-4.46 (m, 1H), 4.42 (s, 3H), 3.90-3.80 (m, 1H), 3.56-3.50 (m, 1H), 2.86 (s, 3H), 2.46-2.37 (m, 2H); ESI MS m/z 366 [M+H].

Sources & evidence

ORD record
ord-8ed3fba374d24601aa62a615edf79385
Source dataset
uspto-grants-2015_03
Patent number
US08987252B2

Reaction notes

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