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Hexylamine → HCID 178444844, compound

HRID 1898446
Notes
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Reaction equation

HRID 1898446 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[NH:22][C:21]2[C:16]3[N:17]=[C:18]([CH3:20])[O:19][C:15]=3[C:14]([C:23]([OH:25])=O)=[CH:13][C:12]=2[N:11]=1.S(Cl)(Cl)=O.[CH2:30]([NH2:36])[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].CCN(C(C)C)C(C)C>C1C=CC=CC=1.C1COCC1>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[NH:9][C:10]1[NH:22][C:21]2[C:16]3[N:17]=[C:18]([CH3:20])[O:19][C:15]=3[C:14]([C:23]([NH:36][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[O:25])=[CH:13][C:12]=2[N:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8102HexylamineHCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 178432356HCID 178432356, compound

Product 1

HCID 178444844HCID 178444844, compoundYield 32.9%

Reagents, catalysts & solvents 2

HCID 241
Benzene
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-[(2,6-dichlorophenyl)amino]-2-methyl-8H-imidazo[4,5-e][1,3]benzoxazole-4-carboxylic acid (Intermediate-55, 0.050 g, 0.132 mmol) in benzene (2 mL) was added thionyl chloride (1.5 mL) at 5-10° C. The reaction mass was refluxed for 3 h. To a solution of hexan-1-amine (0.020 g, 0.198 mmol) in THF (5.0 mL), DIPEA (0.086 g, 0.663 mmol) was added under N2-atmosphere at RT. The solution was stirred for 1 h at RT and above prepared solution was added to reaction mixture. The whole reaction mass was stirred at RT for 1 h. Thionyl chloride was removed under vacuum and stripped out with THF. The reaction mass was quenched in ice water and extracted with ethyl acetate. The organic layer was concentrated. The obtained product was further purified by column chromatography on neutral alumina eluting with 1.5-2.0% MeOH:DCM to afford 0.020 g of the desired product. 1HNMR (DMSO-d6): δ 0.83-0.85 (s, 3H), 1.26 (s, 6H), 1.51-1.54 (m, 2H), 2.61 (s, 3H), 3.30 (m, 2H), 7.30 (s, 1H), 7.57 (s, 3H), 7.90 (s, 1H), 9.30 (s, 1H), 11.40-11.50 (s, 1H); MS [M+H]+: 460.41

Workup

  1. temperatureThe reaction mass was refluxed for 3 h
  2. customabove prepared solution
  3. additionwas added to reaction mixture
  4. stirringThe whole reaction mass was stirred at RT for 1 h
  5. customThionyl chloride was removed under vacuum
  6. customThe reaction mass was quenched in ice water
  7. extractionextracted with ethyl acetate
  8. concentrationThe organic layer was concentrated
  9. customThe obtained product was further purified by column chromatography on neutral alumina eluting with 1.5-2.0% MeOH

Sources & evidence

ORD record
ord-d2b39de9962540418c0f9ba721b394d3
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08519149B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes