Cyclopropylamine → HCID 60631838, compound

HRID 1690495Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[CH:11]1([NH2:14])[CH2:13][CH2:12]1>>[CH:11]1([NH:14][C:2]2[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=2)[CH2:13][CH2:12]1

Participants

Reactant 2

HCID 69828Cyclopropylamine

HCID 8176205-Bromo-2-nitropyridine

Product 1

HCID 60631838HCID 60631838, compound

Procedure

Using analogous procedures to those described in the portion of Note [9] immediately above that is concerned with the preparation of starting materials, 5-bromo-2-nitropyridine (0.41 g) was reacted with cyclopropylamine (0.21 ml) to give 5-cyclopropylamino-2-nitropyridine (0.322 g); 1H NMR: (CDCl3) 0.62 (m, 2H), 0.91 (m, 2H), 2.57 (m, 1H), 4.96 (br s, 1H), 7.19 (m, 1H), 7.99 (d, 1H), 8.16 (m, 1H); which in turn was converted into 5-(N-tert-butoxycarbonyl-N-cyclopropylamino)-2-nitropyridine (0.48 g); 1H NMR: (CDCl3) 0.59 (m, 2H), 1.05 (m, 2H), 1.53 (s, 9H), 3.02 (m, 1H), 8.05 (m, 1H), 8.22 (d, 1H), 8.64 (m, 1H); which in turn was converted into 2-amino-5-(N-tert-butoxycarbonyl-N-cyclopropylamino) pyridine (0.349 g); 1H NMR: (CDCl3) 0.5 (m, 2H), 0.79 (m, 2H), 1.44 (s, 9H), 2.95 (m, 1H), 4.39 (br s, 2H), 6.46 (d, 1H), 7.24 (m, 1H), 7.87 (m, 1H); Mass Spectrum: M+H+ 250; and which in turn was converted into N-[5-(N-tert-butoxycarbonyl-N-cyclopropylamino) pyridin-2-yl]-2-[4-(6,7-dimethoxyquinazolin-4-yloxy)phenyl]acetamide; Mass Spectrum: M+H+ 572.

Sources & evidence

ORD record: ord-b80908636c8649f28e112a2a12c5e1d8
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153643B2

Reaction notes

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