Trifluoroacetic acid → HCID 70144271, compound

HRID 2400301Notes

Reaction equation

F[CH2:2][CH2:3][N:4]1[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.FC(F)(F)C(O)=[O:43]>O1CCOCC1>[C:3]([N:4]1[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:36])([F:35])[F:37])=[CH:18][N:17]=3)=[C:11]([O:38][CH3:39])[CH:10]=2)[CH2:5]1)(=[O:43])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

As shown in Scheme 2, a mixture of intermediate 1 of Scheme 2 (16 mg) and intermediate 3 of Scheme 1 (1-(3-(4-amino-3-methoxyphenylamino)azetidin-1-yl)ethanone, 20 mg) 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 (12 mg) as a TFA salt. 1H-NMR (DMSO-d6, 400 MHz) δ 10.6 (s, 1H), 10.15 (s, 1H), 9.45 (s, 1H), 8.62 (br, 1H), 6.96-7.85 (m, 4H), 6.55 (dd, J=2, 10 Hz, 1H), 6.23 (d, J=10 Hz, 1H), 5.74 (d, J=10 Hz, 1H), 3.15-3.85 (m, 6H), 1.77 (s, 3H); calculated mass for C26H26F3N7O3: 541.2. found: 542.2 (M+H+).

Workup

concentrationThe crude was concentrated under reduced pressure
custompurified

Sources & evidence

ORD record: ord-af0a812d0e0b45dd988ffe0521cd9b4d
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796255B2

Reaction notes

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