Sodium Bicarbonate → HCID 11775359, compound

HRID 1765027Notes

Reaction equation

HRID 1765027 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][C:9]1[N:18]=[C:17]([NH:19][CH2:20][CH2:21][OH:22])[C:16]2[C:15]3[CH:23]=[CH:24][N:25]([CH3:26])[C:14]=3[C:13](I)=[CH:12][C:11]=2[N:10]=1.[S:28]1[CH:32]=[CH:31][CH:30]=[C:29]1B(O)O.C(=O)(O)[O-].[Na+]>COCCOC.C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][C:9]1[N:18]=[C:17]([NH:19][CH2:20][CH2:21][OH:22])[C:16]2[C:15]3[CH:23]=[CH:24][N:25]([CH3:26])[C:14]=3[C:13]([C:29]3[S:28][CH:32]=[CH:31][CH:30]=3)=[CH:12][C:11]=2[N:10]=1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 27339602-Thiopheneboronic acidHCID 21106322HCID 21106322, compound

Product 1

HCID 11775359HCID 11775359, compound

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 2-(3-amino-6-iodo-7-methyl-7H-pyrrolo[3,2-f]quinazolin-1-ylamino)-ethanol trifluoroactic acid salt (90 mg, 0.23 mmol) in ethylene glycol dimethyl ether (8.0 mL) and ethanol (4.0 mL) at 25° C. was treated with thiophene-2-boronic acid (60 mg, 0.47 mmol), a 2.0 M aqueous sodium bicarbonate solution (2.0 mL), and tetrakis(triphenylphosphine)-palladium (0) (5.0 mg). The resulting mixture was heated to reflux for 18 h. The resulting mixture was concentrated in vacuo and the residue suspended in acetonitrile and water and filtered. HPLC purification (21.2 mm×100 mm Zorbax CombiHT column using a 5:95 to 95:5 acetonitrile:water: 0.75% TFA gradient over 15 minutes) afforded 2-(3-amino-7-methyl-6-thiophen-2-yl-7H-pyrrolo[3,2-f]quinazolin-1-ylamino)-ethanol trifluoro-acetic acid salt as a light yellow solid; LRMS for C17H17N5O (M+H)+ at m/z=340.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 18 h
  3. concentrationThe resulting mixture was concentrated in vacuo
  4. filtrationwater and filtered
  5. customHPLC purification (21.2 mm×100 mm Zorbax CombiHT column

Sources & evidence

ORD record
ord-bd696ea324b24d45b1487cb602133867
Source dataset
uspto-grants-2007_06
Patent number
US07226915B2

Reaction notes

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