Trifluoroacetic acid → HCID 131726124, compound

HRID 724636Notes

Reaction equation

HRID 724636 reaction equation
COC1C=CC(C[N:8]2[CH2:13][CH2:12][C:11]3[CH:14]=[C:15]([CH:17]4[S:21](=[O:23])(=[O:22])[NH:20][C:19](=[O:24])[CH2:18]4)[S:16][C:10]=3[CH:9]2[CH2:25][NH:26][C:27]([C:29]2[NH:30][C:31]3[C:36]([CH:37]=2)=[CH:35][C:34]([F:38])=[CH:33][CH:32]=3)=[O:28])=CC=1.C([SiH](C(C)C)C(C)C)(C)C.[F:51][C:52]([F:57])([F:56])[C:53]([OH:55])=[O:54]>C1(C)C=CC=CC=1>[F:51][C:52]([F:57])([F:56])[C:53]([OH:55])=[O:54].[O:23]=[S:21]1(=[O:22])[CH:17]([C:15]2[S:16][C:10]3[CH:9]([CH2:25][NH:26][C:27]([C:29]4[NH:30][C:31]5[C:36]([CH:37]=4)=[CH:35][C:34]([F:38])=[CH:33][CH:32]=5)=[O:28])[NH:8][CH2:13][CH2:12][C:11]=3[CH:14]=2)[CH2:18][C:19](=[O:24])[NH:20]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 138754Silane, tris(1-methylethyl)-HCID 58746870HCID 58746870, compound

Product 1

HCID 131726124HCID 131726124, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 411-G of Example 4.11 (11 mg, 13 μmol) and triisopropylsilane (250 mL, 1.2 mmol) in trifluoroacetic acid (1.3 mL) was heated in a microwave at 170° C. for four minutes. The reaction mixture was diluted with toluene (5 mL) and evaporated. This was repeated until a residue appeared which was purified by preparative LCMS to yield the desired product (1.6 mg, 18%). 1H NMR (500 MHz, CD3OD): δ 7.46 (dd, J=8.8, 4.4 Hz, 1H), 7.32 (dd, J=9.3, 2.0 Hz, 1H), 7.19 (s, 1H), 7.14 (s, 1H), 7.08–7.04 (s, 1H), 5.44 (dd, J=8.8, 8.3 Hz, 1H), 4.03–3.98 (m, 1H), 3.98–3.84 (m, 2H), 3.79–3.70 (m, 1H), 3.52–3.42 (m, 1H), 3.41–3.39 (m, 1H), 3.33–3.27 (m, 1H), 3.13–3.01 (m, 3H); LCMS found for C20H20FN4O4S2 (M+H)+: m/z=463.

Workup

  1. customevaporated
  2. customwas purified by preparative LCMS

Sources & evidence

ORD record
ord-acf322cefa8a4033bc877586c4a87a80
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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