3-Methoxypropyne → HCID 86670379, compound

HRID 1972519Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:22]([OH:31])([C:27]([F:30])([F:29])[F:28])[C:23]([F:26])([F:25])[F:24])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1.[CH2:32]([O:35][CH3:36])[C:33]#[CH:34]>>[F:24][C:23]([F:26])([F:25])[C:22]([C:4]1[CH:5]=[CH:6][C:7]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[C:2]([C:34]#[C:33][CH2:32][O:35][CH3:36])[CH:3]=1)([OH:31])[C:27]([F:30])([F:29])[F:28]

Participants

Reactant 2

HCID 693933-Methoxypropyne

HCID 86670331HCID 86670331, compound

Product 1

HCID 86670379HCID 86670379, compound

Procedure

Following the procedure outlined for Example 152, 2-(3-Bromo-4-(4-(thiophen-2-ylsulfonyl)piperazin-1-yl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (Example 69) was coupled to methyl propargyl ether (Aldrich, St. Louis, Mo.) to afford 1,1,1,3,3,3-hexafluoro-2-(3-(3-methoxyprop-1-ynyl)-4-(4-(thiophen-2-ylsulfonyl)piperazin-1-yl)phenyl)propan-2-ol. 1H NMR (400 MHz, DMSO-d6) δ 8.71 (s, 1H), 8.10 (dd, J=1.00, 4.90 Hz, 1H), 7.69 (dd, J=0.88, 3.62 Hz, 1H), 7.54-7.60 (m, 2H), 7.33 (dd, J=4.01, 4.79 Hz, 1H), 7.12 (d, J=8.80 Hz, 1H), 4.30 (s, 2H), 3.27-3.30 (m, J=5.10 Hz, 4H), 3.23 (s, 3H), 3.10 (d, J=4.30 Hz, 4H); m/z (ESI, +ve ion) 543.2 (M+H)+. GK-GKRP IC50 (Binding)=0.363 μM. GK-GKRP EC50 (LC MS/MS-2)=0.675 μM.

Sources & evidence

ORD record: ord-e8dbd09d9bf04432955ac3a52531c4b3
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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