Morpholine → HCID 46208939, compound

HRID 555819Notes

Reaction equation

HRID 555819 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-73fb78d5242a43a2ad73cf47fa18bb71
Source dataset
uspto-grants-2011_11
Patent number
US08053438B2

Reaction notes

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