Trifluoroacetic acid → HCID 70143467, compound

HRID 2400302Notes

Reaction equation

[C:1]([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)(=[O:3])C.FCCN1CC(NC2C=CC(NC3N=[C:59](NC4C=C(NC(=O)C=C)C=CC=4)[C:58]([C:73](F)(F)F)=[CH:57]N=3)=C(OC)C=2)C1.FC(F)(F)C(O)=[O:82]>O1CCOCC1>[C:30]([NH:29][C:25]1[CH:24]=[C:23]([NH:22][C:20]2[C:19]([C:34]([F:35])([F:37])[F:36])=[CH:18][N:17]=[C:16]([NH:15][C:12]3[CH:13]=[CH:14][C:9]([NH:8][CH:6]4[CH2:7][N:4]([C:1]([O:3][C:58]([CH3:73])([CH3:59])[CH3:57])=[O:82])[CH2:5]4)=[CH:10][C:11]=3[O:38][CH3:39])[N:21]=2)[CH:28]=[CH:27][CH:26]=1)(=[O:33])[CH:31]=[CH2:32]

Participants

Conditions

Temperature: 50 °C

Procedure

As shown in Scheme 2, a mixture of intermediate 1 of Scheme 2 (16 mg) and intermediate 1 of Scheme 1 (tert-butyl 3-(4-amino-3-methoxyphenylamino)azetidine-1-carboxylate, 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 (10 mg) as a TFA salt. 1H-NMR (DMSO-d6, 400 MHz) δ 10.1 (s, 1H), 8.4 (br, 1H), 8.20 (s, 1H), 8.05 (s, 1H), 7.62 (br, 1H), 7.43 (br, 1H), 7.23-7.26 (m, 2H), 6.25 (dd, J=4, 10 Hz, 1H), 6.10-6.14 (m, 1H), 5.72 (d, J=10 Hz, 1H), 5.72 (d, J=10 Hz, 1H), 3.67-4.03 (m, 5H), 3.52-3.55 (m, 2H), 1.35 (s, 9H); calculated mass for C29H32F3N7O4: 599.3. found: 600.3 (M+H+).

Workup

concentrationThe crude was concentrated under reduced pressure
custompurified

Sources & evidence

ORD record: ord-b0a183c0d32d498db923411b8862b872
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796255B2

Reaction notes

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