4-Amino-1-methylpiperidine → HCID 25253676, compound

HRID 1880852Notes

Reaction equation

HRID 1880852 reaction equation
[CH:1]1([N:6]2[CH2:12][C:11]([F:14])([F:13])[C:10](=[O:15])[N:9]([CH3:16])[C:8]3[CH:17]=[N:18][C:19]([NH:21][C:22]4[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[C:24]([F:31])[CH:23]=4)=[N:20][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:56][N:57]1[CH2:62][CH2:61][CH:60]([NH2:63])[CH2:59][CH2:58]1>>[CH:1]1([N:6]2[CH2:12][C:11]([F:13])([F:14])[C:10](=[O:15])[N:9]([CH3:16])[C:8]3[CH:17]=[N:18][C:19]([NH:21][C:22]4[CH:30]=[CH:29][C:25]([C:26]([NH:63][CH:60]5[CH2:61][CH2:62][N:57]([CH3:56])[CH2:58][CH2:59]5)=[O:27])=[C:24]([F:31])[CH:23]=4)=[N:20][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 27375314-Amino-1-methylpiperidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67117789HCID 67117789, compound

Product 1

HCID 25253676HCID 25253676, compound

Procedure

The title compound was synthesized from 4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-2-fluorobenzoic acid as described in the General procedure for amide bond synthesis using HATU and 1-methylpiperidin-4-amine. The final compound was purified by reverse phase HPLC and basified to give the free base 1H NMR (400 MHz, DMSO-d6) δ ppm 1.44-1.74 (m, 11 H) 1.86-2.09 (m, 5 H) 2.15 (s, 3 H) 2.63-2.81 (m, 2 H) 3.57-3.79 (m, 1 H) 3.94-4.16 (m, 2 H) 4.81 (t, J=8.1 Hz, 1 H) 7.32-7.46 (m, 1 H) 7.51 (t, J=8.6 Hz, 1 H) 7.85 (br. s., 1 H) 7.88 (dd, J=4.3, 2.3 Hz, 1 H) 8.30 (s, 1 H) 9.88 (s, 1 H). [M+H] calc'd for C26H32F3N7O2, 532; found 532.

Workup

  1. customas described in the General procedure for amide bond synthesis
  2. customThe final compound was purified by reverse phase HPLC
  3. customto give the free base 1H NMR (400 MHz, DMSO-d6) δ ppm 1.44-1.74 (m, 11 H) 1.86-2.09 (m, 5 H) 2.15 (s, 3 H) 2.63-2.81 (m, 2 H) 3.57-3.79 (m, 1 H) 3.94-4.16 (m, 2 H) 4.81 (t, J=8.1 Hz, 1 H) 7.32-7.46 (m, 1 H) 7.51 (t, J=8.6 Hz, 1 H) 7.85 (br. s., 1 H) 7.88 (dd, J=4.3, 2.3 Hz, 1 H) 8.30 (s, 1 H) 9.88 (s, 1 H)

Sources & evidence

ORD record
ord-7235f6c00edc4eea9311d3579f886ba0
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

Loading…