HCID 71164616, compound → HCID 23648431, compound

HRID 1182300Notes

Reaction equation

HRID 1182300 reaction equation
[OH:1][C@H:2]([C@@H:14]([NH:19][C:20](=[O:43])[O:21][C@H:22]([CH2:27][N:28]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=2)=[N:29]1)[C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:15][CH2:16][CH2:17][CH3:18])[CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)(=[O:7])=[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)CNS(C1C=CC=CN=1)(=O)=O>>[N:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[S:5]([NH:4][CH2:3][C:2]([C@@H:14]([NH:19][C:20](=[O:43])[O:21][C@H:22]([CH2:27][N:28]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:40])[F:41])=[CH:35][CH:34]=2)=[N:29]1)[C:23]([CH3:25])([CH3:26])[CH3:24])[CH2:15][CH2:16][CH2:17][CH3:18])=[O:1])(=[O:6])=[O:7]

Participants

3

Reactant 2

HCID 71164616HCID 71164616, compoundHCID 71164617HCID 71164617, compound

Product 1

HCID 23648431HCID 23648431, compound

Procedure

(1S)-2,2-Dimethyl-1-({3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)propyl (1S)-1-{[(2-pyridinylsulfonyl)amino]acetyl}pentylcarbamate was prepared as in example 3g (27% yield) except that (3S)-1-(1,3-benzothiazol-2-yl)-4,4-dimethylpyrrolidinyl (1S)-1-{(1S)-1-hydroxy-2-[(2-pyridinylsulfonyl)amino]ethyl}pentylcarbamate & (3S)-1-(1,3-benzothiazol-2-yl)-4,4-dimethylpyrrolidinyl (1S)-1-{(1R)-1-hydroxy-2-[(2-pyridinylsulfonyl)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 8.67 (d, J=6 Hz, 1H), 8.13–8.03 (m, 2H), 7.88 (d, J=8 Hz, 1H), 7.77 (d, J=8 Hz, 2H), 7.65 (dd, J=7 Hz, J=5 Hz, 1H), 7.45 (d, J=8 Hz, 1H), 7.27 (t, J=8 Hz, 1H), 7.04 (t, J=8 Hz, 1H), 4.89 (d, J=4 Hz, 1H), 4.15-3.95 (m, 5H), 3.53–3.40 under DMSO peak (m, 2H), 1.60 (m, 1H), 1.42 (m, 1H), 1.23 (m, 4H), 1.09 (s, 3H), 1.06 (s, 3H), 0.82 (m, 3H); ES-LCMS m/z 560 (M+H); HRMS C26H33N5O5S2 m/z 560.2001 (M+Na)+Cal; 560.2010 (M+Na)+.

Sources & evidence

ORD record
ord-d110f9ff43bd4832904a74aab3378966
Source dataset
uspto-grants-2007_10
Patent number
US07288541B2

Reaction notes

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