Hydrochloric Acid → N-[3-[(3S)-3-((4-Fluorophenyl)methyl]piperidinyl]propyl]-N'-[4-(1-methyl-1H-tetrazol-5-yl)phenyl]-urea

HRID 395371Notes

Reaction equation

HRID 395371 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]2[CH2:14][CH2:13][CH2:12][N:11]([CH2:15][CH2:16][CH2:17][NH2:18])[CH2:10]2)=[CH:4][CH:3]=1.C1([O:25][C:26](=O)[NH:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]3[N:38]([CH3:39])[N:37]=[N:36][N:35]=3)=[CH:30][CH:29]=2)C=CC=CC=1.Cl.C(OCC)C>C(#N)C.C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]2[CH2:14][CH2:13][CH2:12][N:11]([CH2:15][CH2:16][CH2:17][NH:18][C:26]([NH:27][C:28]3[CH:29]=[CH:30][C:31]([C:34]4[N:38]([CH3:39])[N:37]=[N:36][N:35]=4)=[CH:32][CH:33]=3)=[O:25])[CH2:10]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 22973281[4-(1-methyl-1H-tetrazol-5-yl)-phenyl]-carbamic acid phenyl esterHCID 697448723-[(3S)-3-[(4-fluorophenyl)methyl]piperidinyl]propylamine

Product 1

HCID 59041104N-[3-[(3S)-3-((4-Fluorophenyl)methyl]piperidinyl]propyl]-N'-[4-(1-methyl-1H-tetrazol-5-yl)phenyl]-urea

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 25 mg 3-[(3S)-3-[(4-fluorophenyl)methyl]piperidinyl]propylamine (0.1 mmol, 1 eq) in 1 ml of dry acetonitrile was added 32.5 mg [4-(1-methyl-1H-tetrazol-5-yl)-phenyl]-carbamic acid phenyl ester (0.1 mmol, 1.1 eq). This mixture was stirred at room temperature for two hours, then concentrated in-vacuo to a pale yellow oil. This oil was purified via radial chromatography, eluting with a 19:1 mixture of methylene chloride and methanol, to yield a white solid. This solid was dissolved in methylene chloride and treated with 1 M hydrochloric acid in diethyl ether (0.1 ml, 1 eq). This mixture was stirred for 30 minutes, then concentrated in-vacuo to a white solid. This solid was dissolved in a 1:1 mixture of acetonitrile and water, and lyophilized to 26 mg of a white solid as product. NMR (300 MHz, CD3OD) δ 7.72 (d, 2H, J=9 Hz), 7.64 (d, 2H, J=9 Hz), 7.21-7.16 (m, 2H), 7.01 (dd, 2 H, J=8, 17 Hz), 4.17 (s, 3H), 3.59-3.54 (m, 1H), 3.40-3.11 (m, 4H), 2.89-2.81 (m, 1H), 2.73-2.59 (m, 3H), 2.10-1.70 (m, 7H), 1.43-1.34 (m, 1H). MS (ESI+) 452 (M−Cl).

Workup

  1. concentrationconcentrated in-vacuo to a pale yellow oil
  2. customThis oil was purified via radial chromatography
  3. washeluting with a 19:1 mixture of methylene chloride and methanol
  4. customto yield a white solid
  5. stirringThis mixture was stirred for 30 minutes
  6. concentrationconcentrated in-vacuo to a white solid
  7. dissolutionThis solid was dissolved in a 1:1 mixture of acetonitrile and water

Sources & evidence

ORD record
ord-4b513c74b1fc49e6b88ae06f5326c09d
Source dataset
uspto-grants-2003_08
Patent number
US06605623B1

Reaction notes

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