Carbon dioxide methanol → HCID 68156462, compound

HRID 537559Notes

Reaction equation

HRID 537559 reaction equation
[CH3:1][C:2]1([CH3:39])[CH2:5][CH:4]([CH:6]([NH:23][C:24]2[CH:25]=[N:26][C:27]([N:30]3[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[N:31]3)=[N:28][CH:29]=2)[C:7]2[CH:22]=[CH:21][C:10]([C:11]([NH:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:12])=[CH:9][CH:8]=2)[CH2:3]1.C(=O)=O.CO>>[CH3:39][C:2]1([CH3:1])[CH2:5][CH:4]([CH:6]([NH:23][C:24]2[CH:29]=[N:28][C:27]([N:30]3[CH:34]=[C:33]([C:35]([F:37])([F:38])[F:36])[CH:32]=[N:31]3)=[N:26][CH:25]=2)[C:7]2[CH:8]=[CH:9][C:10]([C:11]([NH:13][CH:14]=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:12])=[CH:21][CH:22]=2)[CH2:3]1.[CH3:39][C:2]1([CH3:1])[CH2:5][CH:4]([CH:6]([NH:23][C:24]2[CH:29]=[N:28][C:27]([N:30]3[CH:34]=[C:33]([C:35]([F:37])([F:38])[F:36])[CH:32]=[N:31]3)=[N:26][CH:25]=2)[C:7]2[CH:8]=[CH:9][C:10]([C:11]([NH:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:12])=[CH:21][CH:22]=2)[CH2:3]1

Participants

4

Reactant 2

HCID 21973728Carbon dioxide methanolHCID 68156462HCID 68156462, compound

Product 2

HCID 68156462HCID 68156462, compoundHCID 131731954HCID 131731954, compound

Procedure

(+/−)-ethyl 3-(4-((3,3-dimethylcyclobutyl)(2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyrimidin-5-ylamino)methyl)benzamido)propanoate was resolved by chiral SFC (Column: Chiralpak IA. Dimensions: 10 mm×25 cm. Mobile Phase: 65/35 CO2/methanol. Flow Rate: 10.0 mL/min. Modifier: none) to give ethyl 3-(4-((3,3-dimethylcyclobutyl)(2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyrimidin-5-ylamino)methyl)benzamido)propenoate Isomer 1 (retention time: 3.42 min) and ethyl 3-(4-((3,3-dimethylcyclobutyl)(2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyrimidin-5-ylamino)methyl)benzamido)propanoate, Isomer 2 (retention time: 4.55 min). Isomer 1: 1H NMR (400 MHz, CDCl3) δ 8.64 (s, 1H), 7.97 (s, 2H), 7.88 (s, 1H), 7.79-7.64 (m, 2H), 7.41-7.31 (m, 2H), 6.82 (t, J=5.9 Hz, 1H), 4.22 (d, J=9.4 Hz, 1H), 4.16 (q, J=7.0 Hz, 2H), 3.80-3.64 (m, 2H), 2.61 (t, J=5.9 Hz, 2H), 2.58-2.45 (m, 1H), 2.05-1.97 (m, 1H), 1.75-1.63 (m, 2H), 1.63-1.55 (m, 1H), 1.26 (t, J=7.2 Hz, 3H), 1.13 (s, 3H), 1.09 (s, 3H). MS (M+1): 545.4. Isomer 2: 1H NMR (400 MHz, CDCl3) δ 8.64 (s, 1H), 7.97 (s, 2H), 7.88 (s, 1H), 7.80-7.67 (m, 2H), 7.43-7.30 (m, 2H), 6.82 (t, J=6.0 Hz, 1H), 4.22 (d, J=9.4 Hz, 1H), 4.16 (q, J=7.2 Hz, 2H), 3.77-3.64 (m, 2H), 2.63 (t, J=5.7 Hz, 2H), 2.58-2.40 (m, 1H), 2.05-1.97 (m, 1H), 1.76-1.64 (m, 2H), 1.64-1.52 (m, 1H), 1.26 (t, J=7.1 Hz, 3H), 1.13 (s, 3H), 1.09 (s, 3H). MS (M+1): 545.4.

Sources & evidence

ORD record
ord-2c5a8e76fdf347c2a3d729dc2c23f405
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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