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

HRID 2363685Notes

Reaction equation

HRID 2363685 reaction equation
[OH:1][CH2:2][C@H: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)CC.NC[C@@H](O)[CH2:36][OH:37]>>[OH:37][CH2:36][C@H:2]([OH:1])[CH2:3][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

Participants

3

Reactant 2

HCID 6994409(2R)-3-aminopropane-1,2-diolHCID 46910588(2R)-2-[[8-isopropyl-4-[[4-(2-pyridyl)phenyl]methylamino]pyrazolo[1,5-a][1,3,5]triazin-2-yl]amino]butan-1-ol

Product 1

HCID 46910677(R)-2-(1,2-dihydroxypropan-3-ylamino)-8-isopropyl-4-[4-(pyridin-2-yl)benzylamino]pyrazolo[1,5-a]-1,3,5-triazineYield 35%

Procedure

According to the same conditions resulting in the preparation of the compound 2, the compound 10 is prepared from IIa.2 by oxidation reaction of the sulfur atom and then introduction of commercial (R)-3-amino-1,2-propanediol. Yield=35%. Oil. 1H NMR (300 MHz, CDCl3): δ 8.69 (d, 1H, J=4.5 Hz, Harom), 7.98 (d, 2H, J=8.3 Hz, Harom), 7.79-7.70 (m, 2H, Harom) 7.66 (s, 1H, Harom), 7.45 (d, 2H, J=8.3 Hz, Harom), 7.27.28-7.22 (m, 1H, Harom), 6.80 (bs, 1H, NB), 4.78 (d, 2H, J=5.8 Hz, CH2), 3.83-3.79 (m, 1H, CH), 3.65-3-3.55 (m, 4H, 2 CH2), 3.03 (hept, 1H, J=7.0 Hz, CH), 1.28 (d, 6H, J=7.0 Hz, 2 CH3). MS (BSI): m/z 434 (MH+).

Sources & evidence

ORD record
ord-cb055a4c0f5c49f68a9a9d312bc7c95f
Source dataset
uspto-grants-2014_04
Patent number
US08691982B2

Reaction notes

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