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Hydrochloric Acid → 21-Chloro-10-oxa-2,19,23,24-tetrazatetracyclo[18.3.1.13,7.111,15]hexacosa-1(23),3,5,7(26),11,13,15(25),20(24),21-nonaene

HRID 1614966
Notes
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Reaction equation

HRID 1614966 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]2[N:16]=[C:15]([NH:17][CH2:18][CH2:19][CH2:20][C:21]3[CH:22]=[C:23]([OH:27])[CH:24]=[CH:25][CH:26]=3)[C:14]([Cl:28])=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1.[OH-].[Na+].Cl>O1CCCC1.O>[Cl:28][C:14]1[CH:13]=[N:12][C:11]2=[N:16][C:15]=1[NH:17][CH2:18][CH2:19][CH2:20][C:21]1[CH:22]=[C:23]([O:27][CH2:2][CH2:3][C:4]3[CH:5]=[C:6]([NH:10]2)[CH:7]=[CH:8][CH:9]=3)[CH:24]=[CH:25][CH:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58467888HCID 58467888, compound

Product 1

HCID 4686474621-Chloro-10-oxa-2,19,23,24-tetrazatetracyclo[18.3.1.13,7.111,15]hexacosa-1(23),3,5,7(26),11,13,15(25),20(24),21-nonaeneYield 11%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of 3-{3-[(2-{[3-(2-bromoethyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]propyl}phenol (50.0 mg, 0.108 mmol) in tetrahydrofuran (1.0 mL) was added a solution of sodium hydroxide in water (1.0 mL, 1.0 M). The resultant solution was stirred at rt for 60 hours until the reaction was complete. The reaction mixture was neutralized with HCl (3 M aqueous solution) to pH=7. The aqueous layer was extracted with EtOAc three times. The combined organic layers were dried over Na2SO4, filtered, and concentrated to give the crude, which was purified by silica gel column chromatography to give the desired product as a white powder (4.5 mg, 11%). LCMS for C21H22ClN4O (M+H)+: m/z=381.0. 1H NMR (400 MHz, CD3OD): δ 7.98 (s, 1H), 7.92 (s, 1H), 7.48 (d, J=7.6 Hz, 1H), 7.40 (m, 1H), 7.06 (m, 1H), 6.97 (s, 1H), 6.70 (d, J=2.4 Hz, 1H), 6.62 (m, 2H), 3.60 (m, 4H), 3.20 (m, 2H), 2.68 (t, J=7.6 Hz, 2H), 2.02 (t, J=7.6 Hz, 2H).

Workup

  1. extractionThe aqueous layer was extracted with EtOAc three times
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude, which
  6. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fed1cec749944667b9b441390aa4c4a5
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08765727B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes