HCID 69512887, compound → HCID 23648439, compound

HRID 1182292Notes

Reaction equation

HRID 1182292 reaction equation
[OH:1][C@H:2]([C@@H:13]([NH:18][C:19](=[O:42])[O:20][C@H:21]([CH2:26][N:27]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=2)=[N:28]1)[C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:14][CH2:15][CH2:16][CH3:17])[CH2:3][NH:4][C:5]([N:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)=[O:6].O[C@@H]([C@@H](NC(=O)O[C@H](CN1C=CC(C2C=CC(C(F)(F)F)=CC=2)=N1)C(C)(C)C)CCCC)CNC(N1CCOCC1)=O.O[C@H]([C@@H](NC(=O)O[C@H](CN1C=CC(C2C=CC(C(F)(F)F)=CC=2)=N1)C(C)(C)C)CCCC)CNS(C1C=CC=CN=1)(=O)=O.O[C@@H]([C@@H](NC(=O)O[C@H](CN1C=CC(C2C=CC(C(F)(F)F)=CC=2)=N1)C(C)(C)C)CCCC)CNS(C1C=CC=CN=1)(=O)=O>>[N:7]1([C:5]([NH:4][CH2:3][C:2]([C@@H:13]([NH:18][C:19](=[O:42])[O:20][C@H:21]([CH2:26][N:27]2[CH:31]=[CH:30][C:29]([C:32]3[CH:33]=[CH:34][C:35]([C:38]([F:39])([F:41])[F:40])=[CH:36][CH:37]=3)=[N:28]2)[C:22]([CH3:24])([CH3:23])[CH3:25])[CH2:14][CH2:15][CH2:16][CH3:17])=[O:1])=[O:6])[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1

Participants

5

Reactant 4

HCID 69512887HCID 69512887, compoundHCID 71164605HCID 71164605, compoundHCID 71164616HCID 71164616, compoundHCID 71164617HCID 71164617, compound

Product 1

HCID 23648439HCID 23648439, compoundYield 50%

Procedure

(1S)-2,2-Dimethyl-1-({3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)propyl (1S)-1-{[(4-morpholinylcarbonyl)amino]acetyl}pentylcarbamate was prepared (50% yield) as in example 3g except that (1S)-2,2-dimethyl-1-({3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)propyl (1S)-1-{(1 S)-1-hydroxy-2-[(4-morpholinylcarbonyl)amino]ethyl}pentylcarbamate & (1S)-2,2-dimethyl-1-({3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)propyl (1S)-1-{(1R)-1-hydroxy-2-[(4-morpholinylcarbonyl)amino]ethyl}pentylcarbamate were substituted for (1S)-2,2-dimethyl-1-({3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)propyl (1S)-1-{(1S)-1-hydroxy-2-[(2-pyridinylsulfonyl)amino]ethyl}pentylcarbamate & (1S)-2,2-dimethyl-1-({3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)propyl (1S)-1-{(1R)-1-hydroxy-2-[(2-pyridinylsulfonyl)amino]ethyl}pentylcarbamate. 1H-NMR (300 MHz, DMSO-d6): δ 8.00 (d, J=8 Hz, 2H), 7.74 (m, 3H), 7.47 (d, J=8 Hz, 1H), 6.81–6.72 (m, 2H), 4.87 (d, J=9 Hz, 1H), 4.48 (m, 1H), 4.22 (m, 1H), 3.88-3.75 (m, 2H), 3.53 (t, J=4 Hz, 4H), 3.38 under water peak (m, 1H), 3.24 (t, J=4 Hz, 4H), 1.55 (m, 1H), 1.33 (m, 1H), 1.15–0.85 (m, 13H), 0.72 (t, J=6 Hz, 3H); ES-LCMS m/z 596 (M+H); HRMS C29H40N5O5F3 m/Z 596.3060 (M+H)+Cal; 596.3047 (M+H)+.

Sources & evidence

ORD record
ord-aa39452e2d994d20bde2845b731b0ead
Source dataset
uspto-grants-2007_10
Patent number
US07288541B2

Reaction notes

Loading…