Methylamine → 4-amino-N-methyl-1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidine-4-carboxamide

HRID 1775050Notes

Reaction equation

HRID 1775050 reaction equation
C(OC([NH:8][C:9]1([C:42](O)=[O:43])[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[C:29]4[C:24](=[CH:25][N:26]=[C:27]([C:30]5[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=5)[CH:28]=4)[N:23](C4CCCCO4)[N:22]=3)[N:16]=2)[CH2:11][CH2:10]1)=O)(C)(C)C.[CH3:45][NH2:46]>>[NH2:8][C:9]1([C:42]([NH:46][CH3:45])=[O:43])[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[C:29]4[C:24](=[CH:25][N:26]=[C:27]([C:30]5[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=5)[CH:28]=4)[NH:23][N:22]=3)[N:16]=2)[CH2:11][CH2:10]1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 712533374-(tert-Butoxycarbonylamino)-1-(6-(5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidine-4-carboxylic acid

Product 1

HCID 712537784-amino-N-methyl-1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidine-4-carboxamideYield 24%

Procedure

Following the procedures of Example 229, and starting with 4-(tert-butoxycarbonylamino)-1-(6-(5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidine-4-carboxylic acid and methylamine, were reacted and purified via reverse phase HPLC using a gradient of MeCN in water with 0.1% HCOOH to afford 19 mg (24%) of 236 over two steps. ESI MS m/z 429.2 (M+1). 1H NMR (400 MHz, DMSO): 13.95 (s, 1H), 9.22 (d, J=8.4 Hz, 2H), 8.92 (s, 1H), 8.61 (s, 1H), 8.41 (d, J=7.6 Hz, 1H), 8.28 (s, 1H), 8.13 (s, 1H), 7.72 (t, J=7.9 Hz, 1H), 7.52 (d, J=7.6 Hz, 2H), 6.96 (d, J=8.3 Hz, 1H), 6.49 (s, 1H), 4.27 (d, J=13.0 Hz, 2H), 3.53 (t, J=12.5 Hz, 2H), 2.67 (s, 3H), 2.29 (m, 2H), 1.87-1.73 (m, 2H).

Workup

  1. customwere reacted
  2. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-1fcb78d19cc24bca9e05c2344f6fad1b
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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