Dimethylformamide → HCID 178440306, compound

HRID 1625235

Reaction equation

HRID 1625235 reaction equation
[CH:1]1[NH:8][C:6](=[O:7])[NH:5][C:3](=[O:4])[C:2]=1C(O)=O.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.[CH:35]([C:38]1[C:46]2[C:41](=[N:42][CH:43]=[CH:44][C:45]=2[C:47]2[CH:48]=[N:49][C:50]3[C:55]([CH:56]=2)=[CH:54][CH:53]=[CH:52][CH:51]=3)[N:40]([C:57]2[CH:64]=[CH:63][C:60]([C:61]#[N:62])=[C:59]([NH:65][CH:66]3[CH2:71][CH2:70][NH:69][CH2:68][CH2:67]3)[CH:58]=2)[N:39]=1)([CH3:37])[CH3:36].CN([CH:75]=[O:76])C>O.C(OCC)(=O)C>[OH:7][C:6]1[N:8]=[C:1]([C:75]([N:69]2[CH2:68][CH2:67][CH:66]([NH:65][C:59]3[CH:58]=[C:57]([N:40]4[C:41]5=[N:42][CH:43]=[CH:44][C:45]([C:47]6[CH:48]=[N:49][C:50]7[C:55]([CH:56]=6)=[CH:54][CH:53]=[CH:52][CH:51]=7)=[C:46]5[C:38]([CH:35]([CH3:37])[CH3:36])=[N:39]4)[CH:64]=[CH:63][C:60]=3[C:61]#[N:62])[CH2:71][CH2:70]2)=[O:76])[CH:2]=[C:3]([OH:4])[N:5]=1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 903011,2,3,4-Tetrahydro-2,4-dioxo-5-pyrimidinecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 675014474-{3-Isopropyl-4-(quinolin-3-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-2-(piperidin-4-ylamino)benzonitrile

Product 1

HCID 178440306HCID 178440306, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Isoorotic acid (0.021 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.029 g), and 1-hydroxybenzotriazole monohydrate (0.016 g) were added to a solution of compound (77a) (0.050 g) in DMF (1.0 mL), followed by stirring under argon flow at room temperature for 15 hr. The reaction solution was distributed between ethyl acetate and water, and the organic layer was washed with saturated saline. The organic layer after the washing was dried over anhydrous sodium sulfate, and the solvent was distilled away to obtain 2-{1-(2,6-dihydroxypyrimidine-4-carbonyl)piperidin-4-ylamino}-4-{3-isopropyl-4-(quinolin-3-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}benzonitrile, which was used in the subsequent reaction without being purified. According to Example 1(7), compound (78) (0.026 g, the second stage yield: 39%) was prepared as a white solid using 2-{1-(2,6-dihydroxypyrimidine-4-carbonyl)piperidin-4-ylamino}-4-{3-isopropyl-4-(quinolin-3-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}benzonitrile instead of compound (1f).

Workup

  1. washthe organic layer was washed with saturated saline
  2. dry with materialThe organic layer after the washing was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled away

Sources & evidence

ORD record
ord-8cca2535026f4100835c785f066ac0cd
Source dataset
uspto-grants-2014_07
Patent number
US08779142B2

Linked notes

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