Hydrochloric Acid → HCID 136367008, compound

HRID 2062342Notes

Reaction equation

HRID 2062342 reaction equation
[ClH:1].CCOCC.[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[C:9]=1[C:15]1[N:24]=[C:23]([N:25]2[CH2:29][CH2:28][C@@H:27]([NH:30][C:31]([CH:33]3[CH2:35][CH2:34]3)=[O:32])[CH2:26]2)[C:22]2[C:17](=[CH:18][C:19]([CH3:36])=[CH:20][CH:21]=2)[N:16]=1>C(Cl)Cl>[ClH:1].[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[C:9]=1[C:15]1[N:24]=[C:23]([N:25]2[CH2:29][CH2:28][C@@H:27]([NH:30][C:31]([CH:33]3[CH2:34][CH2:35]3)=[O:32])[CH2:26]2)[C:22]2[C:17](=[CH:18][C:19]([CH3:36])=[CH:20][CH:21]=2)[N:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 136121424HCID 136121424, compound

Product 1

HCID 136367008HCID 136367008, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 2 M HCl solution in ether (0.16 mL, 0.32 mmol) was added to a solution of N-((R)-1-(2-(2-fluoro-6-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-yl)cyclopropanecarboxamide (133 mg, 0.32 mmol) in CH2Cl2 (4 mL) under an N2 atmosphere. Additional ether was then added (15 mL) and the reaction mixture was stirred for an hour. The formed precipitate was then filtered and dried to afford N-((R)-1-(2-(2-fluoro-6-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-yl)cyclopropanecarboxamide hydrochloride (135 mg, 95%). LC/MS: m/z 407.5 (M+H)+ at 2.07 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)). 1H NMR (400 MHz, DMSO-d6) δ 8.32 (d, J=7.6 Hz, 1H), 7.56-7.58 (m, 2H), 7.43-7.49 (m, 1H), 6.83-6.88 (m, 2H), 3.94-4.41 (m, 5H), 2.52 (s, 3H), 2.25-2.36 (m, 1H), 1.91-2.13 (m, 1H), 1.47-1.54 (m, 1H), 0.63-0.69 (m, 4H)

Workup

  1. filtrationThe formed precipitate was then filtered
  2. customdried

Sources & evidence

ORD record
ord-ebaeb3ab0ea14451ad0956a33668ede3
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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