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Triethylamine → N-[(1S,1aR,7bR)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromen-1-yl]-N'-(5-fluoro-2-pyridinyl)urea

HRID 751574
Notes
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Reaction equation

HRID 751574 reaction equation
[F:1][C:2]1[C:11]2[O:10][CH2:9][C@H:8]3[C@@H:12](C(O)=O)[C@H:7]3[C:6]=2[C:5]([F:16])=[CH:4][CH:3]=1.C([N:19]([CH2:22]C)CC)C.[NH2:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][N:26]=1.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:39])=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[C:11]2[O:10][CH2:9][C@H:8]3[C@@H:12]([NH:19][C:22]([NH:24][C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][N:26]=4)=[O:39])[C@H:7]3[C:6]=2[C:5]([F:16])=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 27377012-Amino-5-fluoropyridineHCID 21304923(1S,1aR,7bS)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-1-carboxylic acid

Product 1

HCID 60077565N-[(1S,1aR,7bR)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromen-1-yl]-N'-(5-fluoro-2-pyridinyl)urea

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

(1S,1aR,7bS)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-1-carboxylic acid (50 mg, 0.22 mmol, ee ˜90%) was mixed with toluene (1 ml), triethylamine (0.034 ml, 1.1 eq), 2-amino-5-fluoropyridine (28 mg, 1.1 eq), DPPA (0.054 ml, 1.1 eq). The reaction mixture was then heated at stirring at 110° C. for 3 h. The reaction mixture was concentrated by rotary evaporation and purified by column chromatography on silica (50 g, ethylacetate/hexane 1:1) to give 30 mg of the product as white solid.

Workup

  1. temperatureThe reaction mixture was then heated
  2. concentrationThe reaction mixture was concentrated by rotary evaporation
  3. custompurified by column chromatography on silica (50 g, ethylacetate/hexane 1:1)

Sources & evidence

ORD record
ord-88b338c1d8f24e26b842e031008e859d
Source dataset
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07405310B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes