Sodium Hydroxide → HCID 73442183, compound

HRID 1049840Notes

Reaction equation

HRID 1049840 reaction equation
[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([NH:11][C:12]3[C:13]4[C:20]([C:21]([OH:23])=O)=[CH:19][NH:18][C:14]=4[N:15]=[CH:16][N:17]=3)=[CH:10][C:4]=2[S:3]1.[CH3:24][N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C(P1(=O)OP(=O)(CCC)OP(=O)(CCC)O1)CC.C(N(C(C)C)C(C)C)C.[OH-].[Na+]>O.CN(C)C=O>[CH3:24][N:25]1[CH2:30][CH2:29][N:28]([C:21]([C:20]2[C:13]3[C:12]([NH:11][C:9]4[CH:8]=[CH:7][C:5]5[NH:6][C:2](=[O:1])[S:3][C:4]=5[CH:10]=4)=[N:17][CH:16]=[N:15][C:14]=3[NH:18][CH:19]=2)=[O:23])[CH2:27][CH2:26]1

Participants

8

Reactant 5

HCID 14798Sodium HydroxideHCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 73442132HCID 73442132, compound

Product 1

HCID 73442183HCID 73442183, compoundYield 46.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture comprising 18.7 mg (57 μmol) 4-[(2-Oxo-2,3-dihydro-1,3-benzothiazol-6-yl)amino]-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid (prepared according to example 3), 0.64 mL N,N-dimethylformamide, 57.2 mg 1-methylpiperazine, 136 μL 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide solution (50% in ethyl acetate) and 29.9 μL N-ethyl-N-isopropylpropan-2-amine was stirred at 23° C. for 2 days. Water was added, the solution was neutralized by addition of sodium hydroxide solution, the solvents were removed and the residue purified by chromatography to give 10.9 mg (44%) of the title compound.

Workup

  1. customthe solvents were removed
  2. customthe residue purified by chromatography

Sources & evidence

ORD record
ord-fa54ec8fc97f40f39ba5c7f83c95f7a2
Source dataset
uspto-grants-2016_07
Patent number
US09382255B2

Reaction notes

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