Water → HCID 131732589, compound

HRID 876364Notes

Reaction equation

HRID 876364 reaction equation
[CH3:1][N:2]1[CH2:8][CH2:7][CH:6]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]2[CH:16]=[CH:17][C:18]([C:20]3[N:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[CH:19][C:4]=2[CH2:3]1.[C:26]([OH:35])(=[O:34])[C@@H:27]([C@H:29]([C:31]([OH:33])=[O:32])[OH:30])[OH:28].O>CO>[C:31]([CH:29]([CH:27]([C:26]([OH:35])=[O:34])[OH:28])[OH:30])([OH:33])=[O:32].[CH3:1][N:2]1[CH2:8][CH2:7][CH:6]([O:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:5]2[CH:16]=[CH:17][C:18]([C:20]3[N:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[CH:19][C:4]=2[CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 444305L-Tartaric acidHCID 25156308HCID 25156308, compound

Product 1

HCID 131732589HCID 131732589, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the aryloxybenzazepine (52 mg, 0.16 mmol) from Step B above in methanol (1 mL) was added L-tartaric acid (23.5 mg, 0.16 mmol) followed by slow addition of water (5 mL). The resultant solution was lyophilized overnight to give (−)-2-methyl-5-phenoxy-8-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[c]azepine, tartrate salt (70 mg, 93%, AUC HPLC>99%) as a white solid: mp 98-100° C.; 1H NMR (CD3OD, 500 MHz) δ 9.17 (d, J=5.0 Hz, 1H), 8.21-8.18 (m, 2H), 8.08 (d, J=8.0 Hz, 1H), 7.82-7.79 (m, 1H), 7.68 (d, J=8.0 Hz, 1H), 7.28-7.25 (m, 2H), 7.06 (d, J=7.9 Hz, 2H), 6.95 (t, J=7.4 Hz, 1H), 5.75 (d, J=8.0 Hz, 1H), 4.92-4.84 (m, 1H), 4.51-4.48 (m, 1H), 4.41 (s, 2H), 3.95-3.85 (m, 1H), 3.57-3.55 (m, 1H), 2.88 (s, 3H), 2.46-2.38 (m, 2H); ESI MS m/z 332 [M+H].

Sources & evidence

ORD record
ord-5729b2d5d85f411ab1526e9d6adb13be
Source dataset
uspto-grants-2015_03
Patent number
US08987252B2

Reaction notes

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