Acetonitrile → HCID 131732908, compound

HRID 2167518Notes

Reaction equation

HRID 2167518 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]23[CH2:17][CH2:16][N:13]([CH2:14][CH2:15]2)[CH2:12][C:11]2[CH:18]=[C:19]([C:22]4[N:27]=[N:26][C:25]([C:28]([NH:30][CH3:31])=[O:29])=[CH:24][CH:23]=4)[CH:20]=[CH:21][C:10]3=2)[CH:5]=[CH:6][C:7]=1[F:8].C(#N)C.[C:35]([OH:44])(=[O:43])[C@@H:36]([C@H:38]([C:40]([OH:42])=[O:41])[OH:39])[OH:37]>O>[C:40]([C@@H:38]([C@H:36]([C:35]([OH:44])=[O:43])[OH:37])[OH:39])([OH:42])=[O:41].[Cl:1][C:2]1[CH:3]=[C:4]([C:9]23[CH2:15][CH2:14][N:13]([CH2:16][CH2:17]2)[CH2:12][C:11]2[CH:18]=[C:19]([C:22]4[N:27]=[N:26][C:25]([C:28]([NH:30][CH3:31])=[O:29])=[CH:24][CH:23]=4)[CH:20]=[CH:21][C:10]3=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 444305L-Tartaric acidHCID 56847761HCID 56847761, compound

Product 1

HCID 131732908HCID 131732908, compoundYield 0.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the product from Step B (19 mg, 43 mmol) acetonitrile (0.5 mL) was added L-tartaric acid (6.5 mg, 43 mmol) in water (2 mL). The resultant solution was lyophilized for 48 hours to give 6-(5-(3-chloro-4-fluorophenyl)-1,3,4,5-tetrahydro-2,5-ethanobenzo[c]azepin-8-yl)-N-methylpyridazine-3-carboxamide, L-tartrate salt (22 mg, 98%, HPLC: 98.8%) as an off-white solid: 1H NMR (400 MHz, CD3OD): δ 8.32 (m, 2H), 8.16 (s, 1H), 7.91 (d, J=8.0 Hz, 1H), 7.53 (d, J=7.2 Hz, 1H), 7.37 (m, 2H), 6.62 (d, J=8.4 Hz, 1H), 4.95 (m, 2H), 4.46 (s, 2H), 3.65-3.34 (m, 4H), 3.06 (s, 3H), 2.84 (m, 2H), 2.50 (m, 2H). ESI MS (m/z): 437 [M′+1].

Sources & evidence

ORD record
ord-2c1d5606826147ea9ea6cb4139660120
Source dataset
uspto-grants-2015_06
Patent number
US09045468B2

Reaction notes

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