Methanesulfonic Acid → HCID 86677089, compound

HRID 1520401Notes

Reaction equation

HRID 1520401 reaction equation
[C:1]([NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=3[F:23])[CH:14]=2)[N:9]=[C:8]([C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[N:7]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:30][S:31]([OH:34])(=[O:33])=[O:32]>C(Cl)Cl.CO>[CH3:30][S:31]([OH:34])(=[O:33])=[O:32].[C:1]([NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=3[F:23])[CH:14]=2)[N:9]=[C:8]([C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[N:7]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 53303365HCID 53303365, compound

Product 1

HCID 86677089HCID 86677089, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

N-tert-butyl-6-(2,4-difluorophenyl)-2-(pyridin-3-yl)quinazolin-4-amine (1.51 g, 3.87 mmol) was dissolved in CH2Cl2/MeOH (20 mL/20 mL). Methanesulfonic acid (0.251 mL, 3.87 mmol) was added to the solution. The volatiles were evaporated in vacuo. The resultant residue was crystallized from EtOH (30 mL) to give 1.35 g of N-tert-butyl-6-(2,4-difluorophenyl)-2-(pyridin-3-yl)quinazolin-4-amine methanesulfonate as a light yellow powder (72%), LCMS m/z=391 (M+1) (Method D) (Retention time=1.91 min). 1H NMR (300 MHz, DMSO) δ 9.52 (s, 1H), 9.01-8.83 (m, 2H), 8.75 (s, 1H), 8.58 (s, 1H), 8.09 (d, J=7.2 Hz, 1H), 8.03-7.85 (m, 2H), 7.83-7.68 (m, 1H), 7.59-7.43 (m, 1H), 7.33 (t, J=7.91 Hz, 1H), 2.31 (s, 3H), 1.66 (s, 9H).

Workup

  1. customThe volatiles were evaporated in vacuo
  2. customThe resultant residue was crystallized from EtOH (30 mL)

Sources & evidence

ORD record
ord-28e17ece39ea4b41832c00503e0b55de
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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