N,N'-Dimethylethylenediamine → HCID 86703902, compound

HRID 1049898Notes

Reaction equation

HRID 1049898 reaction equation
[NH2:1][C:2]1[C:3]2[N:11]=[C:10]([C:12]3[CH:13]=[C:14]([CH:18]=[C:19]([F:21])[CH:20]=3)[C:15]([OH:17])=O)[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.C[NH:23][CH2:24][CH2:25][NH:26][CH3:27].[CH3:28]N(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:1][C:2]1[C:3]2[N:11]=[C:10]([C:12]3[CH:13]=[C:14]([CH:18]=[C:19]([F:21])[CH:20]=3)[C:15]([NH:23][CH2:24][CH2:25][N:26]([CH3:27])[CH3:28])=[O:17])[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 727035203-(4-Aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzoic acid

Product 1

HCID 86703902HCID 86703902, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the same reaction and purification procedure, the acid 3 (100 mg, 0.35 mmol) was reacted with N,N′-dimethylethane-1,2-diamine (CAS 5752-40-9) (0.08 mL, 0.7 mmol), HATU (165 mg, 0.42 mmol) and DIPEA (0.30 mL, 1.8 mmol) in DMF (1 mL) at room temperature to provide 3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-N-(2-(dimethylamino)ethyl)-5-fluorobenzamide 12. LC/MS (ESI+): m/z 355 (M+H). 1H NMR (400 MHz, DMSO) δ 8.69 (t, J=5.5 Hz, 1H), 8.62 (d, J=8.8 Hz, 1H), 8.57 (dd, J=19.4, 10.5 Hz, 2H), 8.44 (s, 1H), 8.27 (d, J=8.8 Hz, 1H), 8.20 (d, J=8.8 Hz, 1H), 8.05 (s, 1H), 7.73 (d, J=9.3 Hz, 1H), 3.43 (dd, J=12.8, 6.6 Hz, 2H), 2.46 (t, J=6.9 Hz, 2H), 2.21 (s, 6H).

Workup

  1. customthe same reaction and purification procedure

Sources & evidence

ORD record
ord-690818fb17a34a88b16adb2306100368
Source dataset
uspto-grants-2016_07
Patent number
US09382241B2

Reaction notes

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