Trifluoroacetic acid → HCID 69092880, compound

HRID 2400303Notes

Reaction equation

C(N1[CH2:7][CH:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[N:21]=[C:20]([NH:22][C:23]4[CH:24]=[C:25]([NH:29][C:30](=[O:33])[CH:31]=[CH2:32])[CH:26]=[CH:27][CH:28]=4)[C:19]([C:34]([F:37])([F:36])[F:35])=[CH:18][N:17]=3)=[C:11]([O:38][CH3:39])[CH:10]=2)[CH2:5]1)(=O)C.C(NC1C=CC(N)=C(OC)C=1)(C)C.FC(F)(F)C(O)=O>O1CCOCC1>[CH:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[N:21]=[C:20]([NH:22][C:23]3[CH:24]=[C:25]([NH:29][C:30](=[O:33])[CH:31]=[CH2:32])[CH:26]=[CH:27][CH:28]=3)[C:19]([C:34]([F:37])([F:35])[F:36])=[CH:18][N:17]=2)=[C:11]([O:38][CH3:39])[CH:10]=1)([CH3:5])[CH3:7]

Participants

Conditions

Temperature: 50 °C

Procedure

As shown in Scheme 2, a mixture of intermediate 1 of Scheme 2 (16 mg) and N1-isopropyl-3-methoxybenzene-1,4-diamine (15 mg, prepared from WO 2006/021548) in dioxane (1.0 mL) with catalytic trifluoroacetic acid was stirred overnight at 50° C. The crude was concentrated under reduced pressure and purified using HPLC (TFA modifier) to give the title compound (8 mg) as a TFA salt. 1H-NMR (DMSO-d6, 400 MHz) δ 10.12 (s, 1H), 8.49 (br, 1H), 8.24 (s, 1H), 8.06 (s, 1H), 7.71 (br, 1H), 7.47 (d, J=6.4 Hz, 1H), 7.23 (m, 3H), 6.44 (dd, J=10.0, 16.8 Hz, 1H), 6.23 (m, 2H), 5.91 (m, 1H), 5.75 (dd, J=1.6, 10.0 Hz, 1H), 5.21 (m, 1H), 3.68 (s, 3H), 1.10 (d, J=6.0 Hz, 1H); calculated mass for C24H25F3N6O2: 486.2. found: 486.9 (M+H+).

Workup

concentrationThe crude was concentrated under reduced pressure
custompurified

Sources & evidence

ORD record: ord-1c4497f8744f4f6e8df4a83d2313205d
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796255B2

Reaction notes

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