Water → HCID 131732586, compound

HRID 876360Notes

Reaction equation

HRID 876360 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH:12]1[CH2:18][CH2:17][NH:16][CH2:15][C:14]2[CH:19]=[C:20]([C:23]3[N:24]=[N:25][CH:26]=[CH:27][CH:28]=3)[CH:21]=[CH:22][C:13]1=2.[C:29]([OH:38])(=[O:37])[C@@H:30]([C@H:32]([C:34]([OH:36])=[O:35])[OH:33])[OH:31].O>CO>[C:34]([CH:32]([CH:30]([C:29]([OH:38])=[O:37])[OH:31])[OH:33])([OH:36])=[O:35].[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH:12]1[CH2:18][CH2:17][NH:16][CH2:15][C:14]2[CH:19]=[C:20]([C:23]3[N:24]=[N:25][CH:26]=[CH:27][CH:28]=3)[CH:21]=[CH:22][C:13]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 444305L-Tartaric acidHCID 68508122HCID 68508122, compound

Product 1

HCID 131732586HCID 131732586, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the product (45 mg, 0.12 mmol) from Step J above in methanol (1 mL) was added L-tartaric acid (17 mg, 0.12 mmol) followed by slow addition of water (5 mL). The resultant solution was lyophilized overnight to give (+)-5-(naphthalen-2-yloxy)-8-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[c]azepine, tartrate salt (58 mg, 94%, AUC HPLC>99%) as white solid: mp 122-124° C.; 1H NMR (CD3OD, 500 MHz) δ 9.18 (d, J=5.0 Hz, 1H), 8.21 (s, 1H), 8.19 (d, J=8.7 Hz, 1H), 8.09 (d, J=8.0 Hz, 1H), 7.81-7.76 (m, 4H), 7.70 (d, J=8.2 Hz, 1H), 7.40 (t, J=8.2 Hz, 1H), 7.37 (s, 1H), 7.34-7.31 (m, 2H), 5.94 (d, J=8.2 Hz, 1H), 4.88-4.81 (m, 1H), 4.60-4.56 (m, 1H), 4.40 (s, 2H), 3.98-3.90 (m, 1H), 3.70-3.60 (m, 1H), 2.92 (s, 3H), 2.54-2.48 (m, 2H); ESI MS m/z 382 [M+H].

Sources & evidence

ORD record
ord-57732359132f4cc2897a52de515a30bf
Source dataset
uspto-grants-2015_03
Patent number
US08987252B2

Reaction notes

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