Isopropylamine → HCID 67501217, compound

HRID 921569Notes

Reaction equation

HRID 921569 reaction equation
C(OC[N:10]1[CH:14]=[C:13]([C:15]2[N:16]=[CH:17][N:18]([C:20]3[CH:25]=[CH:24][N:23]=[C:22]4[N:26]([C:32]5[CH:39]=[CH:38][C:35]([C:36]#[N:37])=[C:34]([NH:40][CH:41]([CH3:43])[CH3:42])[CH:33]=5)[N:27]=[C:28]([CH:29]([CH3:31])[CH3:30])[C:21]=34)[CH:19]=2)[CH:12]=[N:11]1)C1C=CC=CC=1.C(OCN1C=C(C2N=CN(C3C=CN=C4N(C5C(Br)=C(C=CC=5)C#N)N=C(C(C)C)C=34)C=2)C=N1)C1C=CC=CC=1.C(N)(C)C.O[C@H]1CC[C@H](N)CC1.[OH-].[Na+]>C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(Cl)(Cl)Cl>[NH:10]1[CH:14]=[C:13]([C:15]2[N:16]=[CH:17][N:18]([C:20]3[CH:25]=[CH:24][N:23]=[C:22]4[N:26]([C:32]5[CH:39]=[CH:38][C:35]([C:36]#[N:37])=[C:34]([NH:40][CH:41]([CH3:43])[CH3:42])[CH:33]=5)[N:27]=[C:28]([CH:29]([CH3:31])[CH3:30])[C:21]=34)[CH:19]=2)[CH:12]=[N:11]1

Participants

9

Reactant 5

HCID 6363IsopropylamineHCID 14798Sodium HydroxideHCID 67500135HCID 67500135, compound2×HCID 131734931HCID 131734931, compoundHCID 178511715HCID 178511715, compound

Product 1

HCID 67501217HCID 67501217, compoundYield 43%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Conditions

Temperature
70 °C

Procedure

According to Example 1(6), 4-{4-(4-(1-(benzyloxymethyl)-1H-pyrazol-4-yl)-1H-imidazol-1-yl)-3-isopropyl-1H-pyrazolo[3,4-b]pyridin-1-yl}-2-(isopropylamino)benzonitrile (65%) was prepared using compound (143a) and isopropylamine instead of compound (1e) and trans-4-hydroxycyclohexylamine, respectively, and this 4-{4-(4-(1-(benzyloxymethyl)-1H-pyrazol-4-yl)-1H-imidazol-1-yl)-3-isopropyl-1H-pyrazolo[3,4-b]pyridin-1-yl}-2-(isopropylamino)benzonitrile was dissolved in anisole and trifluoroacetic acid, followed by stirring at 70° C. for 3 hr. The reaction solution was distributed between chloroform and a 2 M aqueous sodium hydroxide solution. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled away to obtain 4-{4-(4-(1H-pyrazol-4-yl)-1H-imidazol-1-yl)-3-isopropyl-1H-pyrazolo[3,4-b]pyridin-1-yl}-2-(isopropylamino)benzonitrile, which was used in the subsequent reaction without being purified. Lastly, according to Example 1(7), compound (143) (the second stage yield: 43%) was prepared as a white solid using 4-{4-(4-(1H-pyrazol-4-yl)-1H-imidazol-1-yl)-3-isopropyl-1H-pyrazolo[3,4-b]pyridin-1-yl}-2-(isopropylamino)benzonitrile instead of compound (1f).

Workup

  1. customwas prepared
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled away

Sources & evidence

ORD record
ord-3673356744d443e997d60e7bf0d9974d
Source dataset
uspto-grants-2016_03
Patent number
US09273045B2

Reaction notes

Loading…