1,3-Propanediamine, N1,N1,N3-trimethyl- → HCID 178483532, compound

HRID 77099Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C:14](O)=[O:15])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[C:17]1[NH:21][C:20]2[CH:22]=[CH:23][C:24]([F:26])=[CH:25][C:19]=2[N:18]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:51][N:52]([CH3:58])[CH2:53][CH2:54][CH2:55][NH:56][CH3:57]>ClCCl>[CH3:51][N:52]([CH3:58])[CH2:53][CH2:54][CH2:55][N:56]([CH3:57])[C:14]([CH:11]1[CH2:10][CH2:9][N:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:17]3[NH:21][C:20]4[CH:22]=[CH:23][C:24]([F:26])=[CH:25][C:19]=4[N:18]=3)[CH:4]=2)[CH2:13][CH2:12]1)=[O:15]

Participants

Conditions

Temperature: 35 °C

Procedure

Method H—Step a To a vial with 1-[4-Chloro-3-(5-fluoro-1H-benzoimidazol-2-yl)-phenyl]-piperidine-4-carboxylic acid (obtained as described in general method 3,4, step e) (0.10 g, 0.26 mmol) and HATU (0.10 g, 0.27 mmol) in dichloromethane (2 mL), TEA (0.07 mL, 0.54 mmol) and N,N,N′-trimethyl-1,3-propanediamine (0.32 mmol, 0.05 mL) were added. The reaction mixture was heated at 35° C. overnight, solvent was removed and the crude was purified by PrepHPLC and SCX column to obtain 0.06 g of the title compound (49%).

Workup

customsolvent was removed
customthe crude was purified by PrepHPLC and SCX column

Sources & evidence

ORD record: ord-27ca3a58482c406992ccbeb17b6ca9cb
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835648B2

Reaction notes

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