Diisopropylethylamine → (S)-4-Amino-6-((3-(benzylthio)-1-(4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)amino)pyrimidine-5-carbonitrile

HRID 1052666Notes

Reaction equation

HRID 1052666 reaction equation
[NH2:1][C@H:2]([C:13]1[N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:17](=[O:25])[C:16]2=[CH:26][CH:27]=[CH:28][N:15]2[N:14]=1)[CH2:3][CH2:4][S:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[NH2:29][C:30]1[C:35]([C:36]#[N:37])=[C:34](Cl)[N:33]=[CH:32][N:31]=1.C(N(CC)C(C)C)(C)C>>[NH2:29][C:30]1[C:35]([C:36]#[N:37])=[C:34]([NH:1][C@H:2]([C:13]2[N:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:17](=[O:25])[C:16]3=[CH:26][CH:27]=[CH:28][N:15]3[N:14]=2)[CH2:3][CH2:4][S:5][CH2:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:33]=[CH:32][N:31]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 122782624-Amino-6-chloropyrimidine-5-carbonitrileHCID 90103146(S)-2-(1-Amino-3-(benzylthio)propyl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Product 1

HCID 73774796(S)-4-Amino-6-((3-(benzylthio)-1-(4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)amino)pyrimidine-5-carbonitrileYield 78.6%

Procedure

(S)-2-(1-Amino-3-(benzylthio)propyl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (10 mg, 0.02 mmol) was treated with 4-amino-6-chloropyrimidine-5-carbonitrile (4 mg, 0.03 mmol) and N,N-diisopropylethylamine (24 μl, 0.14 mmol) according to the method described in Example 17. The residue was purified using SP1® Purification System (0% to 100% hexane-ethyl acetate) to obtain 8 mg (66% yield) of the title compound as a yellow solid. Purity 90%.

Workup

  1. customThe residue was purified
  2. customSP1® Purification System (0% to 100% hexane-ethyl acetate)

Sources & evidence

ORD record
ord-ef583b96b9914946a58d26a953c954ab
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

Loading…