2-Methoxyethylamine → HCID 178496027, compound

HRID 1403171Notes

Reaction equation

HRID 1403171 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].[F:6][CH:7]([F:39])[C:8]1[N:12]([C:13]2[N:18]=[C:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[N:16]=[C:15]([O:25][C@H:26]3[CH2:31][CH2:30][C@H:29]([C:32]([OH:34])=O)[CH2:28][CH2:27]3)[CH:14]=2)[C:11]2[CH:35]=[CH:36][CH:37]=[CH:38][C:10]=2[N:9]=1.C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.[H+].CN(C(=[N+](C)C)ON1C2=NC=CC=C2N=N1)C>CN(C)C=O.C(Cl)(Cl)Cl.O>[F:39][CH:7]([F:6])[C:8]1[N:12]([C:13]2[N:18]=[C:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[N:16]=[C:15]([O:25][C@H:26]3[CH2:31][CH2:30][C@H:29]([C:32]([NH:5][CH2:4][CH2:3][O:2][CH3:1])=[O:34])[CH2:28][CH2:27]3)[CH:14]=2)[C:11]2[CH:35]=[CH:36][CH:37]=[CH:38][C:10]=2[N:9]=1

Participants

8

Reactant 4

HCID 80182-MethoxyethylamineHCID 81531DiisopropylethylamineHCID 86686819HCID 86686819, compoundHCID 178525774HCID 178525774, compound

Product 1

HCID 178496027HCID 178496027, compoundYield 44.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a 2-methoxyethanamine (1.9 mg) were added a solution of trans-4-({6-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-2-(morpholin-4-yl)pyrimidin-4-yl}oxy)cyclohexanecarboxylic acid (11.8 mg) and N,N-diisopropylethylamine (10.5 μL) in N,N-dimethylformamide (400 μL), and were added a solution of N-[(dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methylMethanaminium hexafluorophosphoric acid (11.4 mg) in N,N-dimethylformamide (100 μL), followed by stirring at room temperature overnight. To the reaction solution were added water and chloroform, followed by liquid separation, and the organic layer was concentrated under reduced pressure. The residue was subjected to preparative purification with HPLC to obtain trans-4-({6-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-2-(morpholin-4-yl)pyrimidin-4-yl}oxy)-N-(2-methoxyethyl)cyclohexanecarboxamide (5.9 mg).

Workup

  1. customfollowed by liquid separation
  2. concentrationthe organic layer was concentrated under reduced pressure
  3. customThe residue was subjected to preparative purification with HPLC

Sources & evidence

ORD record
ord-b8a989c11bcf4c7ebb11c69ec2a2d366
Source dataset
uspto-grants-2014_12
Patent number
US08912180B2

Reaction notes

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