Trifluoroacetic acid → HCID 68850868, compound

HRID 1984050Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][N:4]([S:7]([C:10]2[CH:11]=[C:12]([CH:26]=[CH:27][C:28]=2[NH:29]CC2C=C(OC)C(OC)=C(OC)C=2)[C:13]([NH:15][CH:16]2[C:21]([CH3:23])([CH3:22])[C@H:20]3[CH2:24][C@:17]2([CH3:25])[CH2:18][CH2:19]3)=[O:14])(=[O:9])=[O:8])[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>>[NH2:29][C:28]1[CH:27]=[CH:26][C:12]([C:13]([NH:15][CH:16]2[C:21]([CH3:22])([CH3:23])[C@H:20]3[CH2:24][C@:17]2([CH3:25])[CH2:18][CH2:19]3)=[O:14])=[CH:11][C:10]=1[S:7]([N:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)(=[O:9])=[O:8]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 68850921HCID 68850921, compound

Product 1

HCID 68850868HCID 68850868, compoundYield 40%

Procedure

3-(Morpholinosulfonyl)-4-(3,4,5-trimethoxybenzylamino)-N-((1S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)benzamide (2.5.AaBa, 0.36 g, 0.00060 mol) was dissolved in trifluoroacetic acid (7 mL, 0.09 mol). The reaction was stirred overnight at room temperature. The reaction was evaporated to dryness and the residue underwent aqueous workup. Prep-HPLC was performed to isolate the desired product, a white, crystalline solid 2H in 40% yield. MS analysis (m+1)=422.6.

Workup

customThe reaction was evaporated to dryness

Sources & evidence

ORD record: ord-14bb488c397e462b872fd76cfdc454f7
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07544676B2

Reaction notes

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