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

HRID 1052667Notes

Reaction equation

HRID 1052667 reaction equation
[NH2:1][C@H:2]([C:12]1[N:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:16](=[O:24])[C:15]2=[CH:25][CH:26]=[CH:27][N:14]2[N:13]=1)[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH2:28][C:29]1[C:34]([C:35]#[N:36])=[C:33](Cl)[N:32]=[CH:31][N:30]=1.C(N(CC)C(C)C)(C)C>>[NH2:28][C:29]1[C:34]([C:35]#[N:36])=[C:33]([NH:1][C@H:2]([C:12]2[N:17]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:16](=[O:24])[C:15]3=[CH:25][CH:26]=[CH:27][N:14]3[N:13]=2)[CH2:3][CH2:4][O:5][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:32]=[CH:31][N:30]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 122782624-Amino-6-chloropyrimidine-5-carbonitrileHCID 118433850(S)-2-(1-Amino-3-phenoxypropyl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Product 1

HCID 73776928(S)-4-Amino-6-((1-(4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)-3-phenoxypropyl)amino)pyrimidine-5-carbonitrileYield 55%

Procedure

(S)-2-(1-Amino-3-phenoxypropyl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one was treated with 4-amino-6-chloropyrimidine-5-carbonitrile (6 mg, 0.02 mmol) and N,N-diisopropylethylamine (16 μl, 0.09 mmol) according to the method described in Example 17. The residue was purified using SP1® Purification System (0% to 50%, dichloromethane-acetonitrile) to obtain 4 mg (55% yield) of the title compound as a yellow solid. Purity 89%.

Workup

  1. customThe residue was purified
  2. customSP1® Purification System (0% to 50%, dichloromethane-acetonitrile)

Sources & evidence

ORD record
ord-9734091608754e97837d60aebb41292b
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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