2-Amino-1-butanol, (+)- → (S)-2-(1-hydroxybut-2-ylamino)-8-isopropyl-4-[4-(pyridin-2-yl)benzylamino]pyrazolo[1,5-a]-1,3,5-triazine

HRID 2363683Notes

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)[CH2:4][CH3:5].N[C@@H](CC)CO>>[OH:1][CH2:2][C@@H: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]([CH3:31])[CH3:32])=[C:9]2[N:8]=1)[CH2:4][CH3:5]

Participants

Reactant 2

HCID 1200842-Amino-1-butanol, (+)-

HCID 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 46910590(S)-2-(1-hydroxybut-2-ylamino)-8-isopropyl-4-[4-(pyridin-2-yl)benzylamino]pyrazolo[1,5-a]-1,3,5-triazineYield 48%

Procedure

According to the same conditions resulting in the preparation of the compound 2, the compound 4 is prepared from IIa.2 by oxidation reaction of the sulfur atom and then introduction of commercial (S)-(+)-2-aminobutanol. Yield=48%. Foam. 1H NMR (300 MHz, CDCl3): δ 8.69 (d, 1H, J=4.1 Hz, Harom), 7.96 (d, 2H, J=7.9 Hz, Harom), 7.78-7.69 (m, 2H, Harom), 7.62 (s, 1H, Harom), 7.42 (d, 2H, J=7.9 Hz, Harom), 7.26-7.21 (m, 1H, Harom), 6.91 (bs, 1H, NH), 5.10 (s, 1H, H exchangeable), 4.75 (d, 2H, J=6.0 Hz, CH2), 3.93 (bs, 1H, CH), 3.83-3.62 (m, 2H, CH2), 3.02 (hept, 1H, J=6.8 Hz, CH), 1.70-1.52 (m, 2H, CH2), 1.27 (d, 6H, J=6.8 Hz, 2 CH3), 1.02 (t, 3H, J=7.4 Hz, CH3). MS (EST): m/z 432 (MH+).

Sources & evidence

ORD record: ord-28e6c2333ae841fa96482ac1da23b2c1
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691982B2

Reaction notes

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