1,1-Dimethylhydrazine → HCID 57424602, compound

HRID 1093197Notes

Reaction equation

HRID 1093197 reaction equation
[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:33])[NH:23][C:24]4[CH:32]=[CH:31][C:27]([C:28]([OH:30])=O)=[CH:26][CH:25]=4)=[CH:17][CH:16]=3)[N:12]=[C:11]3[N:34]([CH:37]([CH2:41][O:42][CH3:43])[CH2:38][O:39][CH3:40])[N:35]=[CH:36][C:10]=13)[CH2:2]2.O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.[CH3:62][N:63]([CH3:65])[NH2:64].Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[CH3:62][N:63]([CH3:65])[NH:64][C:28]([C:27]1[CH:31]=[CH:32][C:24]([NH:23][C:22]([NH:21][C:18]2[CH:19]=[CH:20][C:15]([C:13]3[N:12]=[C:11]4[N:34]([CH:37]([CH2:38][O:39][CH3:40])[CH2:41][O:42][CH3:43])[N:35]=[CH:36][C:10]4=[C:9]([N:3]4[CH2:2][CH:1]5[O:8][CH:5]([CH2:6][CH2:7]5)[CH2:4]4)[N:14]=3)=[CH:16][CH:17]=2)=[O:33])=[CH:25][CH:26]=1)=[O:30]

Participants

7

Reactant 5

HCID 59761,1-Dimethylhydrazine2×HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 27960291-Hydroxybenzotriazole hydrateHCID 66588997HCID 66588997, compound

Product 1

HCID 57424602HCID 57424602, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(3-(4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(1,3-dimethoxypropan-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)phenyl)ureido)benzoic acid (0.11 g, 0.19 mmol), 1-hydroxybenzotriazole hydrate (HOBT, 51 mg, 0.37 mmol), N-methylmorpholine (63 μL, 0.57 mmol), and N,N-dimethylhydrazine (63 μL, 0.57 mmol) in dimethylformamide (3 mL) was treated with N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC, 72 mg, 0.37 mmol). After approximately 20 minutes, additional quantities of N,N-dimethylhydrazine (100 μL) and EDC (100 mg) were added. The mixture was stirred overnight at room temperature and then purified by reverse-phase high performance liquid chromatography using a Phenomenex Prodigy 21 mm×250 mm column, running a gradient elution of 5% acetonitrile/95% of 0.1% aqueous trifluoroacetic acid to 75% acetonitrile to provide 1-{4-[(2,2-dimethylhydrazino)carbonyl]phenyl}-3-(4-{1-[2-methoxy-1-(methoxymethyl)ethyl]-4-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl}phenyl)urea (114 mg, 95%). MS (ES+): 630.3 (M+H)+

Workup

  1. custompurified by reverse-phase high performance liquid chromatography
  2. washa gradient elution of 5% acetonitrile/95% of 0.1% aqueous trifluoroacetic acid to 75% acetonitrile

Sources & evidence

ORD record
ord-8e280f0aa34c436ca473953c7bb51b33
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

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