Tartrate → HCID 131732905, compound

HRID 2167510Notes

Reaction equation

Br[C:2]1[CH:11]=[CH:10][CH:5]2[NH:6][C:7](=[O:9])[O:8][CH:4]2[CH:3]=1.[C:12]([C@@H:15]([C@H:17]([C:19]([O-:21])=[O:20])[OH:18])[OH:16])([O-:14])=[O:13]>>[C:12]([C@@H:15]([C@H:17]([C:19]([OH:21])=[O:20])[OH:18])[OH:16])([OH:14])=[O:13].[O:8]1[CH:4]2[CH:3]=[CH:2][CH:11]=[CH:10][CH:5]2[NH:6][C:7]1=[O:9]

Participants

Reactant 2

HCID 119400Tartrate

HCID 53412216HCID 53412216, compound

Product 1

HCID 131732905HCID 131732905, compound

Procedure

A procedure similar to Step C of Example 14 was used to couple 5-(4-chlorophenyl)-2,5-ethano-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3,4,5-tetrahydro-1H-2-benzoazepine from Step B of Example 14 with 6-bromo-3,3a-dihydrobenzo[d]oxazol-2(7aH)-one. The desired coupling product was obtained and converted to the corresponding L-tartrate salt as in Step C to provide 64544-chlorophenyl)-2,5-ethano-2,3,4,5-tetrahydro-1H-benzo[c]azepin-8-yl)-3,3a-dihydrobenzo[d]oxazol-2(7aH)-one, L-tartrate salt (34 mg, 11%, AUC HPLC >99%) as an off-white solid: 1H NMR (CD3OD, 500 MHz) δ 7.55 (s, 1H), 7.48-7.45 (m, 3H), 7.42 (dd, J=8.5, 2.0 Hz, 1H), 7.38-7.35 (m, 3H), 7.13 (d, J=8.5 Hz, 1H), 6.45 (d, J=8.5 Hz, 1H), 4.91 (s, 2H), 4.43 (s, 2H), 3.68-3.61 (m, 2H), 3.48-3.41 (m, 2H), 2.82-2.78 (m, 2H), 2.49-2.43 (m, 2H); ESI MS m/z 417 [M+H]+. Anal. Calcd. For C25H21ClN2O2.C4H6O6.3H2O: C, 56.09; H, 5.36; N, 4.51. Found: C, 56.42; H, 5.09; N, 4.29.

Workup

customThe desired coupling product was obtained

Sources & evidence

ORD record: ord-2c17c289f6764b94a43b20a6b2396444
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045468B2

Reaction notes

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