4-Amino-1-methylpiperidine → HCID 57955668, compound

HRID 914199Notes

Reaction equation

HRID 914199 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[C:30]([O:31][CH3:32])=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][C:23]=4[F: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[C:30]([O:31][CH3:32])=[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:27])=[CH:24][C:23]=4[F: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 57955621HCID 57955621, compound

Product 1

HCID 57955668HCID 57955668, 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)-3-fluoro-5-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 1.33 (m, 4H) 1.58 (d, J=14.4 Hz, 6H) 1.75 (m, 2H) 1.93 (m, 2H) 1.99 (s, 1H) 2.16 (s, 3H) 2.78 (d, J=10.6 Hz, 2H) 3.29 (s, 3H) 3.83 (s, 2H) 3.89-4.01 (t, J=12 Hz, 2H) 4.32 (m, 1H) 7.24-7.48 (m, 2H) 8.10 (s, 1H) 8.26 (d, J=7.6 Hz, 1H) 8.53 (s, 1H). [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-b24d22860e6b49c8bb714c4c43986953
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

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