Carbon Dioxide → HCID 60152349, compound

HRID 537545Notes

Reaction equation

HRID 537545 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[N:5][N:6]([C:8]2[N:13]=[CH:12][C:11]([NH:14][CH:15]([C:19]3[CH:33]=[CH:32][C:22]([C:23]([NH:25][CH2:26][CH2:27][C:28]([O:30]C)=[O:29])=[O:24])=[CH:21][CH:20]=3)[CH2:16][CH2:17][CH3:18])=[CH:10][N:9]=2)[CH:7]=1.C(=O)=O>>[F:35][C:2]([F:1])([F:34])[C:3]1[CH:4]=[N:5][N:6]([C:8]2[N:13]=[CH:12][C:11]([NH:14][CH:15]([C:19]3[CH:33]=[CH:32][C:22]([C:23]([NH:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[O:24])=[CH:21][CH:20]=3)[CH2:16][CH2:17][CH3:18])=[CH:10][N:9]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 280Carbon Dioxide2×HCID 68156467methyl 3-(4-(1-(2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyrimidin-5-ylamino)butyl)benzamido)propanoate

Product 1

HCID 60152349HCID 60152349, compound

Procedure

The title compound was prepared by a method analogous to that described in Step C of Example 109, using Isomer 2 of methyl 3-(4-(1-(2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyrimidin-5-ylamino)butyl)benzamido)propanoate. 1H NMR (400 MHz, CD3OD, δ): 8.73 (s, 1H), 7.97 (s, 2H), 7.89 (s, 1H), 7.68 (d, J=8.4 Hz, 2H), 7.38 (d, J=8.4 Hz, 2H), 4.40 (t, J=6.8 Hz, 1H), 3.50 (t, J=6.8 Hz, 2H), 2.52 (t, J=6.4 Hz, 2H), 1.67-1.82 (m, 2H), 1.20-1.50 (m, 2H), 0.87 (t, J=7.2 Hz, 3H). MS (M+1) 477.2. Chiral SFC: Chiralpak AD-3, 4.6×150 mm, 3 μm. Modifier: 0.05% DEA. Gradient: 95% CO2/5% methanol linear to 60% CO2/40% methanol over 16.0 minutes. Flow rate: 2.5 mL/min. Retention time: 7.69 minutes, 99.8% ee (Isomer 1).

Sources & evidence

ORD record
ord-3f51c160db61464a9f973e36b26eac1d
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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