4-Amino-1-methylpiperidine → HCID 57955606, compound

HRID 1880997Notes

Reaction equation

HRID 1880997 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]([CH3:31])[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: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]([NH:63][CH:60]5[CH2:61][CH2:62][N:57]([CH3:56])[CH2:58][CH2:59]5)=[O:27])=[C:24]([CH3:31])[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 67117794HCID 67117794, compound

Product 1

HCID 57955606HCID 57955606, 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-methylbenzoic 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 1.36-1.77 (m, 11 H) 1.98 (m, 4 H) 2.16 (s, 3 H) 2.31 (s, 3 H) 2.75 (d, J=11 Hz, 2 H) 3.17 (br. s., 2 H) 3.67 (d, J=7 Hz, 1 H) 4.03 (t, J=14 Hz, 3 H) 4.81 (m, 1 H) 7.22 (d, J=8 Hz, 1 H) 7.46 (d, J=8 Hz, 1 H) 7.68 (br. s., 1 H) 7.99 (d, J=8 Hz, 1 H) 8.25 (s, 1 H) 9.51 (br. s., 1 H). [M+H] calc'd for C27H35F2N7O2, 528; found 528.

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

Sources & evidence

ORD record
ord-9f7bea883ab64d628d86d9e549441ee1
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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