1-(2-Pyridyl)cyclopropylamine Dihydrochloride → HCID 59275647, compound

HRID 1877655Notes

Reaction equation

HRID 1877655 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]2[CH:12]=[CH:13][C:14]3[O:18][C:17]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)=[C:16]([C:26](=[O:29])[NH:27][CH3:28])[C:15]=3[CH:30]=2)[CH:10]=1)[C:5]([OH:7])=O.Cl.Cl.[N:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[C:39]1([NH2:42])[CH2:41][CH2:40]1>O>[F:1][C:2]1[CH:10]=[C:9]([C:11]2[CH:12]=[CH:13][C:14]3[O:18][C:17]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)=[C:16]([C:26]([NH:27][CH3:28])=[O:29])[C:15]=3[CH:30]=2)[CH:8]=[C:4]([C:5](=[O:7])[NH:42][C:39]2([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][N:33]=3)[CH2:41][CH2:40]2)[CH:3]=1

Participants

4

Reactant 2

HCID 533931811-(2-Pyridyl)cyclopropylamine DihydrochlorideHCID 59275659HCID 59275659, compound

Product 1

HCID 59275647HCID 59275647, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The product precipitated from the reaction mixture during the coupling of 3-fluoro-5-(2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)benzoic acid (0.068 mmol scale) with 1-(pyridin-2-yl)cyclopropanamine dihydrochloride (TBTU, iPr2NET, DMF, r.t.). The mixture was diluted with 4 ml H2O, the off white solid filtered and washed with 3×2 ml H2O. The solid was further washed with 3×1 ml MeOH and dried. 1H NMR (500 MHz, DMSO-d6) δ 9.50 (s, 1H), 8.52 (d, J=4.58, 1H), 8.47 (d, J=3.97, 1H), 8.17 (s, 1H), 8.03-8.00 (overlapping m, 3H), 7.83 (overlapping m, 3H), 7.73 (d, 1H), 7.70 (dt overlapping with d, 1H), 7.43-7.40 (overlapping m, 3H), 7.17 (dd, J=6.87, 5.34, 1H), 2.88 (d, J=4.27, 3H), 1.59 (m, 2H), 1.32 (m, 2H). LC/MS were performed by using Shimadzu-VP instrument with UV detection at 220 nm and Waters Micromass. HPLC method: Solvent A=10% MeOH-90% H2O-0.1% TFA, Solvent B=90% MeOH-10% H2O-0.1% TFA, Start % B=0, Final % B=100, Gradient time=2 min, Stop time=3 min, Flow Rate=5 ml/min, Column: Phenomenex-Luna, 3.0×50 mm, S10; (ES+) m/z (M+H)+=524.25, HPLC Rt=1.512 min.

Workup

  1. filtrationthe off white solid filtered
  2. washwashed with 3×2 ml H2O
  3. washThe solid was further washed with 3×1 ml MeOH
  4. customdried
  5. customB=100, Gradient time=2 min
  6. customtime=3 min, Flow Rate=5 ml/min, Column

Sources & evidence

ORD record
ord-f73a67acbe99487285aca18e75b578c1
Source dataset
uspto-grants-2012_11
Patent number
US08309558B2

Reaction notes

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