HCID 71226726, compound → HCID 71233425, compound

HRID 2409935Notes

Reaction equation

HRID 2409935 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[N:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][CH2:12][C@H:11]([NH:15][C@@H:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]3[NH2:22])[CH2:10]2)=[N:7][CH:8]=1.Cl[C:26]1[O:27][C:28]([C:31]2[CH:32]=[C:33]([NH:37][C:38](=[O:42])[O:39][CH2:40][CH3:41])[CH:34]=[CH:35][CH:36]=2)=[CH:29][N:30]=1>>[F:24][C:2]([F:1])([F:23])[C:3]1[N:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][CH2:12][C@H:11]([NH:15][C@@H:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]3[NH:22][C:26]3[O:27][C:28]([C:31]4[CH:32]=[C:33]([NH:37][C:38](=[O:42])[O:39][CH2:40][CH3:41])[CH:34]=[CH:35][CH:36]=4)=[CH:29][N:30]=3)[CH2:10]2)=[N:7][CH:8]=1

Participants

3

Reactant 2

HCID 71226726HCID 71226726, compoundHCID 71233138HCID 71233138, compound

Product 1

HCID 71233425HCID 71233425, compoundYield 21%

Procedure

Ethyl 3-(2-((1R,2R)-2-((S)-1-(5-(trifluoromethyl)pyrazin-2-yl)piperidin-3-ylamino)cyclohexylamino)oxazol-5-yl)phenylcarbamate (7.13 mg, 0.012 mmol, 21% yield) was synthesized as described in General Procedure H using (1R,2R)—N1-((S)-1-(5-(trifluoromethyl)pyrazin-2-yl)piperidin-3-yl)cyclohexane-1,2-diamine (19.86 mg, 0.058 mmol) and Intermediate 44, ethyl 3-(2-chlorooxazol-5-yl)phenylcarbamate (15.42 mg, 0.058 mmol). The product was purified via preparative LC/MS with the following conditions: Column. Waters XBridge C18, 19×100 mm, 5-μm particles; Guard Column: Waters XBridge C18, 19×10 mm, 5-μm particles; Mobile Phase A: 5:95 acetonitrile:water with 0.1% ammonium hydroxide; Mobile Phase B: 95:5 acetonitrile:water with 0.1% ammonium hydroxide; Gradient: 35-75% B over 10 minutes, then a 7-minute hold at 75% B; Flow rate: 20 mL/min. Anal. Calcd. for C28H34F3N7O3 m/z 573.3, found: 574.3 (M+H)+; 1H NMR (500 MHz, DMSO-d6) δ ppm 9.64 (s, 1H), 8.40 (d, J=1.1 Hz, 1H), 8.36 (s, 1H), 7.96 (s, 1H), 7.69 (s, 1H), 7.27-7.18 (m, 3H), 7.15-7.10 (m, 2H), 4.41 (d, J=10.7 Hz, 1H), 4.21 (d, J=12.9 Hz, 1H), 4.13 (q, J=7.2 Hz, 2H), 3.25 (td, J=9.3, 4.0 Hz, 1H), 3.06-2.99 (m, 1H), 2.76-2.69 (m, 1H), 2.66-2.54 (m, 2H), 2.06-1.96 (m, 2H), 1.89-1.82 (m, 1H), 1.75-1.61 (m, 3H), 1.45 (d, J=13.2 Hz, 1H), 1.37-1.28 (m, 2H), 1.28-2.21 (m, 5H), 1.09 (d, J=12.4 Hz, 1H).

Workup

  1. customThe product was purified via preparative LC/MS with the following conditions
  2. customa 7-minute hold

Sources & evidence

ORD record
ord-0a0bef112de14821bef5acacadc50768
Source dataset
uspto-grants-2014_08
Patent number
US08815909B2

Reaction notes

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