1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → N-(6-fluoro-3,4-dihydro-2H-chromen-4-yl)-2-(2-oxo-3,3-diphenylpiperidin-1-yl)acetamide

HRID 1667153Notes

Reaction equation

HRID 1667153 reaction equation
[O:1]=[C:2]1[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][N:3]1[CH2:20][C:21](O)=[O:22].Cl.C(N=C=NCCCN(C)C)C.[F:36][C:37]1[CH:38]=[C:39]2[C:44](=[CH:45][CH:46]=1)[O:43][CH2:42][CH2:41][CH:40]2[NH2:47]>ClCCl>[F:36][C:37]1[CH:38]=[C:39]2[C:44](=[CH:45][CH:46]=1)[O:43][CH2:42][CH2:41][CH:40]2[NH:47][C:21](=[O:22])[CH2:20][N:3]1[CH2:4][CH2:5][CH2:6][C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]1=[O:1]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 162444136-fluoro-3,4-dihydro-2H-1-benzopyran-4-amineHCID 673592802-(2-Oxo-3,3-diphenylpiperidin-1-yl)acetic acid

Product 1

HCID 67443310N-(6-fluoro-3,4-dihydro-2H-chromen-4-yl)-2-(2-oxo-3,3-diphenylpiperidin-1-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(2-oxo-3,3-diphenylpiperidin-1-yl)acetic acid (Example 68E, 0.063 g, 0.204 mmol), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.059 g, 0.305 mmol) and 6-fluorochroman-4-amine (0.037 g, 0.224 mmol) in dichloromethane (0.5 mL) was stirred at room temperature. After stirring for approximately 60 hours, the reaction was loaded directly onto a SF15-12 column (Analogix®, Burlington, Wis.), and the title compound was eluted using a gradient of 5% to 75% ethyl acetate/hexanes over 25 minutes (flow=30 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 7.22-7.31 (m, 2H), 7.15-7.22 (m, 5H), 7.05-7.10 (m, 2H), 6.85-6.94 (m, 3H), 6.75-6.81 (m, 1H), 5.13 (dt, J=8.5, 5.8 Hz, 2H), 4.18 (d, J=14.6 Hz, 1H), 4.10-4.21 (m, 1H), 3.97-4.09 (m, 1H), 4.01 (d, J=14.6 Hz, 1H), 3.54-3.62 (m, 2H), 2.54-2.64 (m, 2H), 2.12-2.25 (m, 1H), 1.91-2.02 (m, 1H), 1.81-1.90 (m, 2H); MS (ESI−) m/z 457 (M−H)−.

Workup

  1. washthe title compound was eluted
  2. customover 25 minutes

Sources & evidence

ORD record
ord-7d92c8a48c42445fbe2d59a9ef09fe74
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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