Fumaric Acid → 2-(1,3-Dihydroxyprop-2-ylamino)-8-isopropyl-4-[4-(pyridin-2-yl)benzylamino]pyrazolo[1,5-a]-1,3,5-triazine fumarate

HRID 2363692Notes

Reaction equation

HRID 2363692 reaction equation
[OH:1][CH2:2][CH:3]([NH:6][C:7]1[N:12]=[C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[CH:17][CH:16]=2)[N:10]2[N:27]=[CH:28][C:29]([CH:30]([CH3:32])[CH3:31])=[C:9]2[N:8]=1)[CH2:4][OH:5].[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37]>CCO.CCOCC>[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37].[OH:1][CH2:2][CH:3]([NH:6][C:7]1[N:12]=[C:11]([NH:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[CH:19][CH:20]=2)[N:10]2[N:27]=[CH:28][C:29]([CH:30]([CH3:32])[CH3:31])=[C:9]2[N:8]=1)[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 469108512-(1,3-Dihydroxyprop-2-ylamino)-8-isopropyl-4-[4-(pyridin-2-yl)benzylamino]pyrazolo[1,5-a]-1,3,5-triazine

Product 1

HCID 469108522-(1,3-Dihydroxyprop-2-ylamino)-8-isopropyl-4-[4-(pyridin-2-yl)benzylamino]pyrazolo[1,5-a]-1,3,5-triazine fumarate

Reagents, catalysts & solvents 1

HCID 21585056Diethyl ether ethanolSolvent

Procedure

The product 17 is treated with fumaric acid in an EtOH/Et2O solution. The fumaric acid salt 18 crystallizes from the reaction medium. Mp=179-181° C. 1H NMR (300 MHz, DMSO-d6): δ 13.11 (bs, 2H, OH), 8.76 (bs, 1H, NH), 8.64 (d, 1H, J=4.5 Hz, Harom), 8.03 (d, 2H, J=8.1 Hz, Harom), 7.94-7.82 (m, 2H, Harom), 7.72 (s, 1H, Harom) 7.49 (bs, 2H, Harom) 7.35-7.31 (m, 1H, Harom), 6.63 (s, 2H, 2 ═CH), 6.33 (d, 1H, J=6.0 Hz, NH), 4.67 (d, 2H, J=6.0 Hz, CH2), 3.98-3.83 (m, 1H, CH), 3.58-3.42 (m, 4H, 2 CH2), 2.91 (hept, 1H, J=7.0 Hz, CH), 1.23 (d, 6H, J=7.0 Hz, 2 CH3).

Workup

  1. customThe fumaric acid salt 18 crystallizes from the reaction medium

Sources & evidence

ORD record
ord-2338ca1cc3674ef196e45d2d24a3c40a
Source dataset
uspto-grants-2014_04
Patent number
US08691982B2

Reaction notes

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