Isopropylamine → HCID 60631570, compound

HRID 1690494Notes

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]([NH2:14])([CH3:13])[CH3:12]>>[CH:11]([NH:14][C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1)([CH3:13])[CH3:12]

Participants

Reactant 2

HCID 6363Isopropylamine

HCID 8176205-Bromo-2-nitropyridine

Product 1

HCID 60631570HCID 60631570, compoundYield 93%

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 was reacted with isopropylamine to give 5-isopropylamino-2-nitropyridine in 93% yield; 1H NMR: (CDCl3) 1.3 (d, 6H), 3.74 (m, 1H), 4.46 (br s, 1H), 6.9 (m, 1H), 7.84 (m, 1H), 8.15 (d, 1H); Mass Spectrum: M+H+ 182; which in turn was converted into 5-(N-tert-butoxycarbonyl-N-isopropylamino)-2-nitropyridine in 84% yield; 1H NMR: (CDCl3) 1.19 (d, 6H), 1.4 (s, 9H), 4.55 (m, 1H), 7.76 (m, 1H), 8.26 (m, 1H), 8.38 (m, 1H); Mass Spectrum: M+H+ 282; which in turn was converted into 2-amino-5-(N-tert-butoxycarbonyl-N-isopropylamino)pyridine in 84% yield; 1H NMR: (CDCl3) 1.05 (d, 6H), 1.36 (br s, 9H), 4.46 (br s, 2H), 6.48 (d, 1H), 7.14 (m, 1H), 7.78 (m, 1H); Mass Spectrum: M+H+ 252; and which in turn was converted into N-[5-(N-tert-butoxycarbonyl-N-isopropylamino)pyridin-2-yl]-2-[4-(6,7-dimethoxyquinazolin-4-yloxy) phenyl]acetamide; Mass Spectrum: M+H+ 560.

Sources & evidence

ORD record: ord-7226692655ac40dbbbb0bfbe4cff3445
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153643B2

Reaction notes

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