Triethylamine → N-[(1S,1aR,7bR)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromen-1-yl]-N'-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]urea

HRID 2182045Notes

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[S:26][CH:27]=[C:28]([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)[N:29]=1.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:44])=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[S:26][CH:27]=[C:28]([C:30]5[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=5)[N:29]=4)=[O:44])[C@H:7]3[C:6]=2[C:5]([F:16])=[CH:4][CH:3]=1

Participants

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-4-(4-chlorophenyl)-1,3-thiazole (52 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 the product was crystallized from ethanol and collected by filtration to give 50 mg of the product as white solid.

Workup

temperatureThe reaction mixture was then heated
concentrationThe reaction mixture was concentrated by rotary evaporation
customthe product was crystallized from ethanol
filtrationcollected by filtration

Sources & evidence

ORD record: ord-6fa89d0a8d984e82a6e23876c2e99d97
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06894177B2

Reaction notes

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