4-Amino-1-methylpiperidine → HCID 57955559, compound

HRID 914228Notes

Reaction equation

HRID 914228 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:23]=[CH:24][C:25]([C:28](O)=[O:29])=[N:26][CH:27]=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.[CH3:55][N:56]1[CH2:61][CH2:60][CH:59]([NH2:62])[CH2:58][CH2:57]1>>[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:23]=[CH:24][C:25]([C:28]([NH:62][CH:59]5[CH2:60][CH2:61][N:56]([CH3:55])[CH2:57][CH2:58]5)=[O:29])=[N:26][CH:27]=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 67117752HCID 67117752, compound

Product 1

HCID 57955559HCID 57955559, compound

Procedure

The title compound was synthesized from 5-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)picolinic 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. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.44-2.04 (m, 13H) 2.77 (d, J=5 Hz, 2H) 3.01-3.22 (m, 2H) 3.34 (s, 3H) 3.47 (d, J=11 Hz, 2H) 4.08 (m, 3H) 4.80 (m, 1H) 7.85-8.02 (m, 1H) 8.30 (s, 1H) 8.44 (dd, J=9, 2 Hz, 1H) 8.69 (d, J=8 Hz, 1H) 8.80-8.92 (m, 1H) 9.85-10.01 (m, 1H). [M+H] calc'd for C25H32F2N8O2, 516. found 516.

Workup

  1. customas described in the general procedure for amide bond synthesis
  2. customThe final compound was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-beff2ebba0344a2aa4a9486885565853
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

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