Morpholine → HCID 46208939, compound

HRID 887406Notes

Reaction equation

HRID 887406 reaction equation
Cl[C:2]1[C:3]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[NH:20][C:19]4[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=4[N:17]=3)=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][N:7]=1.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>CS(C)=O>[O:28]1[CH2:29][CH2:30][N:25]([C:2]2[C:3]([O:8][C:9]3[CH:10]=[CH:11][C:12]([NH:15][C:16]4[NH:20][C:19]5[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=5[N:17]=4)=[CH:13][CH:14]=3)=[N:4][CH:5]=[CH:6][N:7]=2)[CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 8083Morpholine2×HCID 59351261HCID 59351261, compound

Product 1

HCID 46208939HCID 46208939, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

N-(4-(3-chloropyrazin-2-yloxy)phenyl)-1H-benzo[d]imidazol-2-amine (191 mg, 565 μmol) and morpholine (74 μL, 848 μmol) in DMSO was heated to 80° C. After 3 h, starting material remained so additional morpholine (74 uL, 848 umol) was added and the mixture was heated overnight. The hot solution was then poured onto ice water which caused a brown solid to precipitate. The solid was collected by filtration, washed and dried to give the desired product. MS (ESI, pos. ion) m/z: 389.1 (M+1). IC50 (uM) +++++.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated overnight
  3. additionThe hot solution was then poured onto ice water which
  4. customto precipitate
  5. filtrationThe solid was collected by filtration
  6. washwashed
  7. customdried

Sources & evidence

ORD record
ord-5a3a0c497b354931a7166818ec40b11a
Source dataset
uspto-grants-2012_08
Patent number
US08247418B2

Reaction notes

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