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Hydrochloric Acid → HCID 136367008, compound

HRID 2079426
Notes
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Reaction equation

HRID 2079426 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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) ppm.

Workup

  1. filtrationThe formed precipitate was then filtered
  2. customdried

Sources & evidence

ORD record
ord-06637756c96c458eb71c85e5d5a14781
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07928107B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes