Diisopropylethylamine → HCID 69204953, compound

HRID 897943Notes

Reaction equation

HRID 897943 reaction equation
Cl.[I:2][C:3]1[C:11]2[C:6](=[N:7][CH:8]=[N:9][C:10]=2[NH2:12])[N:5]([CH:13]2[CH2:17][CH2:16][NH:15][CH2:14]2)[N:4]=1.[CH:18]1[C:30]2[CH:29]([CH2:31][O:32][C:33]([N:35]([CH3:42])[C:36]([CH3:41])([CH3:40])[C:37](O)=[O:38])=[O:34])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]=2[CH:21]=[CH:20][CH:19]=1.ON1C2N=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C>ClCCl.O>[NH2:12][C:10]1[N:9]=[CH:8][N:7]=[C:6]2[N:5]([CH:13]3[CH2:17][CH2:16][N:15]([C:37](=[O:38])[C:36]([N:35]([CH3:42])[C:33](=[O:34])[O:32][CH2:31][CH:29]4[C:28]5[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=5[C:22]5[C:30]4=[CH:18][CH:19]=[CH:20][CH:21]=5)([CH3:41])[CH3:40])[CH2:14]3)[N:4]=[C:3]([I:2])[C:11]=12

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 4147680Fmoc-N-Me-Aib-OHHCID 223473313-iodo-1-tetrahydro-1H-3-pyrrolyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine hydrochloride

Product 1

HCID 69204953HCID 69204953, compoundYield 125.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of rac-3-iodo-1-tetrahydro-1H-3-pyrrolyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine monohydrochloride (0.100 g, 0.273 mmol) in dichloromethane (5 mL) was added 2-[[(9H-9-fluorenylmethoxy)carbonyl](methyl)amino]-2-methylpropanoic acid (0.120 g, 0.354 mmol), 1-hydroxy-7-azabenzotriazole (0.041 g, 0.30 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.068 g, 0.35 mmol), and diisopropylethyl amine (0.18 g, 0.24 mL, 1.4 mmol). The reaction mixture was stirred at room temperature for 5 h and then poured into water (10 mL). The organic phase was separated and washed with brine (10 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated to afford rac-9H-9-fluorenylmethyl N-{2-[3-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)tetrahydro-1H-1-pyrrolyl]-1,1-dimethyl-2-oxoethyl}-N-methylcarbamate as a yellow solid (0.223 g) which was used in subsequent reactions without further purification. RP-HPLC Rt 13.688 min, 63% purity (5% to 85% acetonitrile/0.1M aqueous ammonium acetate, buffered to pH 4.5, over 20 min at 1 mL/min; λ=254 nm; Deltapak C18, 300 Å, 5 μm, 150×3.9 mm column); m/z 652 (MH+).

Workup

  1. customThe organic phase was separated
  2. washwashed with brine (10 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a28de59308c94e6589c8d1a13c2eafb8
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

Loading…