Diisopropylethylamine → 2-(6-(4-(cyclobutyamino)-7H-pyrrolo[2,3-d]pyrimidine-2-ylamino)-2-oxo-3,4-dihydroquinolin-1(2H)-yl)-N-(2-(dimethylamino)ethyl)acetamide

HRID 2281460Notes

Reaction equation

HRID 2281460 reaction equation
[CH:1]1([NH:5][C:6]2[C:7]3[CH:30]=[CH:29][NH:28][C:8]=3[N:9]=[C:10]([NH:12][C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[N:19]([CH2:23][C:24](O)=[O:25])[C:18](=[O:27])[CH2:17][CH2:16]4)[N:11]=2)[CH2:4][CH2:3][CH2:2]1.CN(C(ON1N=[N:46][C:41]2C=C[CH:44]=[N:45][C:40]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:55]CN(C(C)C)C(C)C.CNN(CC)NC>CN(C=O)C>[CH:1]1([NH:5][C:6]2[C:7]3[CH:30]=[CH:29][NH:28][C:8]=3[N:9]=[C:10]([NH:12][C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[N:19]([CH2:23][C:24]([NH:46][CH2:41][CH2:40][N:45]([CH3:44])[CH3:55])=[O:25])[C:18](=[O:27])[CH2:17][CH2:16]4)[N:11]=2)[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57041336N,N-DimethylaminoethylamineHCID 579903132-(6-(4-(cyclobutyamino)-7H-pyrrolo[2,3-d]pyrimidine-2-ylamino)-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetic acid

Product 1

HCID 579904392-(6-(4-(cyclobutyamino)-7H-pyrrolo[2,3-d]pyrimidine-2-ylamino)-2-oxo-3,4-dihydroquinolin-1(2H)-yl)-N-(2-(dimethylamino)ethyl)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(6-(4-(cyclobutyamino)-7H-pyrrolo[2,3-d]pyrimidine-2-ylamino)-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetic acid 4 mg, 0.01 mmol) in DMF (0.3 mL) was added HATU, DIPEA and N,N-dimethylaminoethylamine. After stirring for 1 h at room temperature, it was then purified by prep HPLC to give 2-(6-(4-(cyclobutyamino)-7H-pyrrolo[2,3-d]pyrimidine-2-ylamino)-2-oxo-3,4-dihydroquinolin-1(2H)-yl)-N-(2-(dimethylamino)ethyl)acetamide (MS calcd for C25H32N8O2 476.3. found [MH] 477.0; UV 205.1, 304.5 nm).

Workup

  1. customit was then purified by prep HPLC

Sources & evidence

ORD record
ord-f7bcefd89acd41c7bd6da5882a39bd4f
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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