Diisopropylethylamine → HCID 57593716, compound

HRID 1785305Notes

Reaction equation

HRID 1785305 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[C:11]([Br:12])=[CH:10][N:9]=[C:8]([NH:13][C:14]2[CH:15]=[C:16]([NH:20][C:21]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[O:22])[CH:17]=[CH:18][CH:19]=2)[N:7]=1.[CH3:28][CH2:29][N:30]([CH:34](C)C)C(C)C.C([S:39]N=C=O)C>CN(C=O)C>[Br:12][C:11]1[C:6]([NH:5][CH2:4][CH2:3][CH2:2][NH:1][C:34]([NH:30][CH2:29][CH3:28])=[S:39])=[N:7][C:8]([NH:13][C:14]2[CH:15]=[C:16]([NH:20][C:21]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[O:22])[CH:17]=[CH:18][CH:19]=2)=[N:9][CH:10]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 21933416HCID 21933416, compoundHCID 57593297HCID 57593297, compound

Product 1

HCID 57593716HCID 57593716, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(3-((4-((3-aminopropyl)amino)-5-bromo-2-pyrimidinyl)amino)phenyl)-1-pyrrolidinecarboxamide (100 mg, 0.20 mmol) and DMF (5 mL) was treated with DIEA (0.1 mL, 0.6 mmol, 3eq) and ethylthioisocyanate (15 mg, 0.17 mmol, 0.9 eq). The resulting mixture was stirred at RT for 2 hr. Then the crude mixture was purified by HPLC using acetonitrile/water to afford the title compound (82 mg).

Workup

  1. customThen the crude mixture was purified by HPLC

Sources & evidence

ORD record
ord-d94129faff384dacbbcf2e6310915cfd
Source dataset
uspto-grants-2009_03
Patent number
US07504410B2

Reaction notes

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