Tetrahydrofuran → HCID 118059386, compound

HRID 2279150Notes

Reaction equation

HRID 2279150 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[C:15]3[N:17]([CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)[N:18]=[C:19]([CH3:20])[C:14]3=[C:13]([CH2:27][N:28]3[CH2:33][C:32]([CH3:35])([CH3:34])[NH:31][CH2:30][C:29]3([CH3:37])[CH3:36])[CH:12]=2)=[CH:7][CH:6]=1.C1COCC1.[N:43]([CH2:46][C:47]([O:49][CH2:50][CH3:51])=[O:48])=[C:44]=[O:45].CCN(C(C)C)C(C)C>O>[CH2:50]([O:49][C:47](=[O:48])[CH2:46][NH:43][C:44]([N:31]1[CH2:30][C:29]([CH3:37])([CH3:36])[N:28]([CH2:27][C:13]2[CH:12]=[C:11]([C:8]3[CH:7]=[CH:6][C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:10][CH:9]=3)[N:16]=[C:15]3[N:17]([CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)[N:18]=[C:19]([CH3:20])[C:14]=23)[CH2:33][C:32]1([CH3:35])[CH3:34])=[O:45])[CH3:51]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 76283Ethyl isocyanatoacetateHCID 81531DiisopropylethylamineHCID 90013940HCID 90013940, compound

Product 1

HCID 118059386HCID 118059386, compoundYield 27.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 200 mg 6-(4-Methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-4-(2,2,5,5-tetramethyl-piperazin-1-ylmethyl)-1H-pyrazolo[3,4-b]pyridine in 3 ml abs. THF were added 51 mg ethyl isocyanatoacetate and 51 mg Hünig's base. After 16 h at rt water was added, and the pH was adjusted to neutral. The mixture was extracted with ethyl acetate twice and the combined organic layers were dried and concentrated in vacuo. 70 mg of the title compound were obtained, which were subjected to the subsequent reaction without further purification.

Workup

  1. extractionThe mixture was extracted with ethyl acetate twice
  2. customthe combined organic layers were dried
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8c8008ef48974da589bfa5cfac8d2563
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

Loading…