Hydrochloric Acid → HCID 136366984, compound

HRID 2062332Notes

Reaction equation

HRID 2062332 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18])[N:6]=[C:5]2[N:19]1[CH2:23][CH2:22][C@@H:21]([NH:24][C:25]([CH:27]2[CH2:29][CH2:28]2)=[O:26])[CH2:20]1.[ClH:30].CCOCC>C(Cl)Cl>[ClH:30].[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18])[N:6]=[C:5]2[N:19]1[CH2:23][CH2:22][C@@H:21]([NH:24][C:25]([CH:27]2[CH2:28][CH2:29]2)=[O:26])[CH2:20]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 136121331HCID 136121331, compound

Product 1

HCID 136366984HCID 136366984, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-((R)-1-(6-fluoro-2-(2-hydroxyphenyl)quinazolin-4-yl)pyrrolidin-3-yl)cyclopropanecarboxamide (225 mg, 0.57 mmol) in 5 mL CH2Cl2 was added a 2 M HCl solution in ether (0.28 mL, 0.57 mmol), which resulted in the precipitation of a solid. After the addition of 20 mL ether, the reaction mixture was stirred for 1 h. The solvents were evaporated under reduced pressure to afford N-((R)-1-(6-fluoro-2-(2-hydroxyphenyl)quinazolin-4-yl)pyrrolidin-3-yl)cyclopropanecarboxamide hydrochloride (225 mg, 91%). LC/MS: m/z 393.3 (M+H)+ at 2.43 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)). 1H NMR (400 MHz, DMSO-d6) δ 8.23 (d, J=8.3 Hz, 1H), 8.04 (d, J=10.6 Hz, 1H), 7.91-7.94 (m, 1H), 7.79-7.83 (m, 1H), 7.44-7.48 (m, 1H), 7.00-7.03 (m, 2H), 4.44 (t, J=4.9 Hz, 1H), 4.09-4.23 (m, 3H), 3.87-3.90 (m, 1H), 2.25-2.34 (m, 1H), 2.02-2.09 (m, 1H), 1.49-1.55 (m, 1H), 0.68-0.71 (m, 4H).

Workup

  1. customresulted in the precipitation of a solid
  2. customThe solvents were evaporated under reduced pressure

Sources & evidence

ORD record
ord-b43098c749084a2d8793af8a89a47b96
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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