4-Amino-1-methylpiperidine → HCID 57955660, compound

HRID 1880998Notes

Reaction equation

HRID 1880998 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]([OH:28])=O)=[C:24]([O:31][CH3:32])[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.[CH3:57][N:58]1[CH2:63][CH2:62][CH:61]([NH2:64])[CH2:60][CH2:59]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:64][CH:61]5[CH2:62][CH2:63][N:58]([CH3:57])[CH2:59][CH2:60]5)=[O:28])=[C:24]([O:31][CH3:32])[CH:23]=4)=[N:20][C:7]2=3)[CH2:2][CH2:3][CH2:4][CH2:5]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 67117824HCID 67117824, compound

Product 1

HCID 57955660HCID 57955660, 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-methoxybenzoic 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 1.48-2.22 (m, 14 H) 2.66-2.88 (m, 2 H) 3.05 (m, 2 H) 3.33 (s, 3 H) 3.46 (d, J=11 Hz, 2 H) 3.86 (s, 3 H) 4.05 (t, J=14 Hz, 3 H) 4.81 (m, 1 H) 7.49 (m, 2 H) 7.64 (m, 1 H) 7.93 (d, J=7 Hz, 1 H) 8.28 (s, 1 H) 9.69 (s, 1 H). [M+H] calc'd for C27H35F2N7O3, 544; found 544.

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-26cca63462204e19ac304d91641f639e
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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