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

HRID 2363686Notes

Reaction equation

HRID 2363686 reaction equation
[OH:1][CH2:2][C@H:3]([OH:32])[CH2:4][NH:5][C:6]1[N:11]=[C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[CH:16][CH:15]=2)[N:9]2[N:26]=[CH:27][C:28]([CH:29]([CH3:31])[CH3:30])=[C:8]2[N:7]=1.[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][C@H:3]([OH:32])[CH2:4][NH:5][C:6]1[N:11]=[C:10]([NH:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[CH:18][CH:19]=2)[N:9]2[N:26]=[CH:27][C:28]([CH:29]([CH3:30])[CH3:31])=[C:8]2[N:7]=1

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 46910677(R)-2-(1,2-dihydroxypropan-3-ylamino)-8-isopropyl-4-[4-(pyridin-2-yl)benzylamino]pyrazolo[1,5-a]-1,3,5-triazine

Product 1

HCID 46910763(R)-2-(1,2-dihydroxypropan-3-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 10 is treated with fumaric acid in an EtOH/Et2O solution. The fumaric acid salt 11 crystallizes from the reaction medium. Mp=168-170° C. 1H NMR (300 MHz, CDCl3 1 drop DMSO-d6): δ 8.64 (d, 1H, J=3.8 Hz, Harom), 7.93 (d, 2H, J=8.1 Hz, Harom), 7.74-7.65 (m, 2H, Harom), 7.60 (s, 1H, Harom), 7.42 (d, 2H, J=8.1 Hz, Harom), 7.26-7.18 (m, 1H, Harom), 6.76 (s, 2H, ═CH), 4.74 (d, 2H, J=5.9 Hz, CH2), 3.80-3.75 (m, 1H, CH), 3.56-3.45 (m, 4H, 2 CH2), 2.99 (hept, 1H, J=6.8 Hz, CH), 1.23 (d, 6H, J=6.8 Hz, 2 CH3).

Workup

  1. customThe fumaric acid salt 11 crystallizes from the reaction medium

Sources & evidence

ORD record
ord-8f6d134a652c4546be1360f904c6af2a
Source dataset
uspto-grants-2014_04
Patent number
US08691982B2

Reaction notes

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