Hydrochloric Acid → HCID 69670110, compound

HRID 81038Notes

Reaction equation

HRID 81038 reaction equation
O1CCOCC1.Cl.[C:8]([C:10]1[C:15]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:18][CH:17]=2)=[CH:14][N:13]=[C:12]([C:29]2[CH:30]=[C:31]([CH:41]=[CH:42][CH:43]=2)[CH2:32][NH:33]C(=O)OC(C)(C)C)[C:11]=1[F:44])#[N:9]>ClCCl>[NH2:33][CH2:32][C:31]1[CH:30]=[C:29]([C:12]2[C:11]([F:44])=[C:10]([C:15]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:18][CH:17]=3)=[CH:14][N:13]=2)[C:8]#[N:9])[CH:43]=[CH:42][CH:41]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66927587Tert-butyl 3-(4-cyano-3-fluoro-5-(4-phenoxyphenyl)pyridin-2-yl)benzylcarbamate

Product 1

HCID 69670110HCID 69670110, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 1 M dioxane solution of HCl (3 mL, 3.00 mmol) was added to a solution of tert-butyl 3-(4-cyano-3-fluoro-5-(4-phenoxyphenyl)pyridin-2-yl)benzylcarbamate (54.6 mg, 0.110 mmol) in dichloromethane (3 mL). After 3 h at room temperature, the mixture was concentrated and pumped under vacuum to give 2-(3-(aminomethyl)phenyl)-3-fluoro-5-(4-phenoxyphenyl)isonicotinonitrile as brown solid, assumed as bis-HCl salt (48 mg, 93% yield). 1H NMR (500 MHz, methanol-d4) δ ppm 8.80 (1H, s), 8.16 (1H, s), 8.08 (1H, br. s), 7.72 (2H, δ, J=8.25 Hz), 7.65 (2H, δ, J=3.85 Hz), 7.42 (2H, t, J=7.70 Hz), 7.20 (1H, t, J=7.29 Hz), 7.16 (2H, δ, J=7.97 Hz), 7.10 (2H, δ, J=7.97 Hz), 4.25 (2H, s); MS (ES+) m/z: 396 (M+H); LC retention time: 3.768 min (analytical HPLC Method A).

Workup

  1. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-cc1200a0bfbf47bfb50bfb445e4cd777
Source dataset
uspto-grants-2014_09
Patent number
US08846673B2

Reaction notes

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