Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 71239514, compound

HRID 2281149Notes

Reaction equation

HRID 2281149 reaction equation
[CH3:1][CH:2]([CH3:26])[CH2:3][CH:4]([C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=O)=[CH:19][CH:18]=1)[NH:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[C:11]([CH3:16])[CH:10]=2.Cl.[CH3:28][O:29][C:30](=[O:34])[CH2:31][CH2:32][NH2:33].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl.CCOC(C)=O>[CH3:28][O:29][C:30](=[O:34])[CH2:31][CH2:32][NH:33][C:21](=[O:23])[C:20]1[CH:19]=[CH:18][C:17]([CH:4]([NH:5][C:6]2[CH:7]=[N:8][C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[C:11]([CH3:16])[CH:10]=3)[CH2:3][CH:2]([CH3:26])[CH3:1])=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 71239490HCID 71239490, compound

Product 1

HCID 71239514HCID 71239514, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[3-Methyl-1-(7-methyl-quinolin-3-ylamino)-butyl]-benzoic acid (44 mg, 0.13 mM) in DCM (1 mL) was added TEA (63.6 mg, 0.629 mM) and followed by 3-amino-propionic acid methyl ester hydrochloric acid (6) (26.4 mg, 0.189 mM) and then HBTU (57.3 mg, 0.151 mM). The reaction was stirred at RT for 16 h. The reaction mixture was diluted with EtOAc (5 mL) and washed with water (2×2 mL). The organic layer was separated, dried over Na2SO4 and concentrated. The crude material was separated by a 12 g silica gel column with 10-100% EtOAc in heptane to afford desired product (49 mg, 90%). 1H NMR (500 MHz, CDCl3) δ ppm 0.98 (d, J=6.10 Hz, 3 H) 1.04 (d, J=6.34 Hz, 3 H) 1.61-1.70 (m, 1 H) 1.71-1.86 (m, 2 H) 2.66 (t, 2 H) 2.82 (s, 3 H) 3.68-3.76 (m, 5 H) 4.36 (d, J=4.88 Hz, 1 H) 4.44-4.54 (m, 1 H) 6.73 (d, J=2.20 Hz, 1 H) 6.80 (t, J=5.49 Hz, 1 H) 7.20 (d, J=8.29 Hz, 1 H) 7.35 (d, J=8.54 Hz, 1 H) 7.45 (d, J=8.29 Hz, 2 H) 7.67 (s, 1 H) 7.75 (d, 2 H) 8.45 (d, J=2.44 Hz, 1 H). LC-MS: 434.2 (M+1).

Workup

  1. washwashed with water (2×2 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude material was separated by a 12 g silica gel column with 10-100% EtOAc in heptane

Sources & evidence

ORD record
ord-b53baabdc0da4c1e97eb07edc19ffdd1
Source dataset
uspto-grants-2015_09
Patent number
US09139538B2

Reaction notes

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