6-chloro-2-N,4-N-dipropyl-1,3,5-triazine-2,4-diamine → HCID 57378018, compound

HRID 530079Notes

Reaction equation

HRID 530079 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[N:5]=[C:4]([NH:12][CH2:13][CH2:14][CH3:15])[N:3]=1.Cl.[F:17][CH:18]([F:22])[CH2:19][O:20][NH2:21]>>[CH2:13]([NH:12][C:4]1[N:5]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[N:7]=[C:2]([NH:21][O:20][CH2:19][CH:18]([F:22])[F:17])[N:3]=1)[CH2:14][CH3:15]

Participants

3

Reactant 2

HCID 183046-chloro-2-N,4-N-dipropyl-1,3,5-triazine-2,4-diamineHCID 45158834O-(2,2-Difluoroethyl)hydroxylamine--hydrogen chloride (1/1)

Product 1

HCID 57378018HCID 57378018, compoundYield 59%

Procedure

2-Chloro-N-(4,6-bis-(n-propylamino)-[1,3,5]triazine (XXXIV) was reacted with O-(2,2-difluoro-ethyl)-hydroxylamine hydrochloride as described in Example 13, affording C in 59% yield. 400 MHz 1H NMR (DMSO-d6, ppm) 9.91-9.56 (1H, m), 7.00-6.90 (1H, m), 6.89-6.67 (1H, m), 6.48-6.13 (1H, m, 4.12-3.98 (2H, m), 3.20-3.09 (4H, m), 1.53-1.41 (4H, m), 0.88-0.80 (6H, m). ESI-MS (m/z) 291 [M+H]+.

Workup

  1. customaffording C in 59% yield

Sources & evidence

ORD record
ord-dbb52a2b6b06410bb1976cd2c7e5ed4b
Source dataset
uspto-grants-2016_05
Patent number
US09351972B2

Reaction notes

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