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

HRID 1052672Notes

Reaction equation

HRID 1052672 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=[C:26]([CH3:29])[CH:27]=[CH:28][N:15]2[N:14]=1)[CH2:3][CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[NH2:30][C:31]1[C:36]([C:37]#[N:38])=[C:35](Cl)[N:34]=[CH:33][N:32]=1.C(N(CC)C(C)C)(C)C>>[NH2:30][C:31]1[C:36]([C:37]#[N:38])=[C:35]([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=[C:26]([CH3:29])[CH:27]=[CH:28][N:15]3[N:14]=2)[CH2:3][CH2:4][O:5][CH2:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:34]=[CH:33][N:32]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 122782624-Amino-6-chloropyrimidine-5-carbonitrileHCID 118433815(S)-2-(1-Amino-3-(benzyloxy)propyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Product 1

HCID 73776930(S)-4-Amino-6-((3-(benzyloxy)-1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)amino)pyrimidine-5-carbonitrileYield 73%

Procedure

(S)-2-(1-Amino-3-(benzyloxy)propyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (24 mg, 0.06 mmol) was treated with 4-amino-6-chloropyrimidine-5-carbonitrile (10 mg, 0.06 mmol), N,N-diisopropylethylamine (59 μl, 0.34 mmol) according to the method described in Example 17. The residue was purified using SP1® Purification System (0% to 80%, hexane-ethyl acetate) to obtain 21 mg (73% yield) of the title compound as a yellow solid. Purity 100%.

Workup

  1. customThe residue was purified
  2. customSP1® Purification System (0% to 80%, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-9ddb9b6f964a48b2966732cdc5e4de6d
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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