Ethyl isocyanate → HCID 90014241, compound

HRID 2279151Notes

Reaction equation

HRID 2279151 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.[CH2:43]([N:45]=[C:46]=[O:47])[CH3:44].CCN(C(C)C)C(C)C>O>[CH2:43]([NH:45][C:46]([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:47])[CH3:44]

Participants

6

Reactant 4

HCID 8022Ethyl isocyanateHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 90013940HCID 90013940, compound

Product 1

HCID 90014241HCID 90014241, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 290 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 41 mg ethyl isocyanate and 75 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. 325 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-8fa0965b53c243e086dcc5148811fa79
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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