Trifluoroacetic acid → HCID 117728069, compound

HRID 1772753Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:12][C:13]1[N:14]=[C:15]2[C:20]([CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[N:19][CH:18]=[C:17]([C:27]3[CH:28]=[CH:29][C:30]([N:33]4[CH2:38][CH2:37][N:36](C(OC(C)(C)C)=O)[CH2:35][CH2:34]4)=[N:31][CH:32]=3)[N:16]2[CH:46]=1.[C:47]([OH:53])([C:49]([F:52])([F:51])[F:50])=[O:48]>>[F:50][C:49]([F:52])([F:51])[C:47]([OH:53])=[O:48].[N:33]1([C:30]2[N:31]=[CH:32][C:27]([C:17]3[N:16]4[CH:46]=[C:13]([CH2:12][O:11][C:2]5[CH:3]=[CH:4][C:5]6[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=6)[N:1]=5)[N:14]=[C:15]4[C:20]([CH:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[N:19][CH:18]=3)=[CH:28][CH:29]=2)[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 117732316HCID 117732316, compound

Product 1

HCID 117728069HCID 117728069, compoundYield 55%

Procedure

Compound 91a (130 mg, 0.210 mmol) was treated with TFA as described in Example 87, Step F to obtain the title compound 83 as a light yellow solid (61.7 mg, 55% yield). 1H-NMR (300 MHz, DMSO-d6) δ (ppm): 8.84 (s, 1H), 8.51 (s, 1H), 8.27 (d, J=9.0 Hz, 1H), 8.13 (s, 1H), 8.03 (dd, J=2.4 Hz, 8.7 Hz, 1H), 7.90 (d, J=8.1 Hz, 1H), 7.86 (s, 1H), 7.81 (d, J=8.7 Hz, 1H), 7.72-7.67 (m, 1H), 7.49-7.44 (m, 1H), 7.12 (d, J=9.0 Hz, 1H), 7.07 (d, J=9.0 Hz, 1H), 5.65 (s, 2H), 4.03-4.00 (m, 2H), 3.87-3.78 (m, 5H), 3.61-3.54 (m, 2H), 3.28-3.20 (m, 4H), 2.01-1.87 (m, 4H). Mass Spectrum (LCMS, ESI pos.) Calcd. for C30H31N7O2: 522.3 (M+H). Found 522.3.

Sources & evidence

ORD record: ord-ebb83bb081fa43c183eda48cf20f33be
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249163B2

Reaction notes

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