4-Amino-1-methylpiperidine → HCID 57955580, compound

HRID 1880975Notes

Reaction equation

HRID 1880975 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]([F:31])[C:23]=4[O:32][CH3:33])=[N:20][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:34][N:35]1[CH2:40][CH2:39][CH:38]([NH2:41])[CH2:37][CH2:36]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:41][CH:38]5[CH2:39][CH2:40][N:35]([CH3:34])[CH2:36][CH2:37]5)=[O:28])=[C:24]([F:31])[C:23]=4[O:32][CH3:33])=[N:20][C:7]2=3)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 27375314-Amino-1-methylpiperidineHCID 57955575HCID 57955575, compound

Product 1

HCID 57955580HCID 57955580, 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-fluoro-3-methoxybenzoic acid and 1-methylpiperidin-4-amine as described in the General procedure for amide bond synthesis. The final compound was purified by reverse phase HPLC and basified to give the free base. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.37-1.66 (m, 7 H) 1.75 (m, 4 H) 1.82-2.04 (m, 4 H) 2.15 (m, 3 H) 2.66-2.81 (m, 2 H) 3.16 (s, 1 H) 3.70 (m, 1 H) 3.90 (s, 3 H) 4.05 (t, J=13.8 Hz, 2 H) 4.77 (m, 1 H) 7.24 (t, J=8.1 Hz, 1 H) 7.96-8.13 (m, 2 H) 8.26 (s, 1 H) 8.35 (s, 1 H). [M+H] calc'd for C27H34F3N7O3, 562; found 562.

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-0f67679f34884a8fadc6a1275c852aa0
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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