Diisopropylethylamine → HCID 86657272, compound

HRID 1403693Notes

Reaction equation

HRID 1403693 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][NH:22][C:23](=O)[O:24]C4C=CC([N+]([O-])=O)=CC=4)[CH2:16][CH2:15]3)[CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[F:44][C:45]([F:54])([F:53])[CH:46]([C:48]1[N:49]=[CH:50][S:51][CH:52]=1)[OH:47]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][NH:22][C:23](=[O:24])[O:47][CH:46]([C:48]4[N:49]=[CH:50][S:51][CH:52]=4)[C:45]([F:44])([F:53])[F:54])[CH2:16][CH2:15]3)[CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 67130392HCID 67130392, compoundHCID 67394652HCID 67394652, compound

Product 1

HCID 86657272HCID 86657272, compoundYield 47.2%

Procedure

The procedure described in Example 4 (step 4.6.) is followed. Starting from 0.183 g (1 mmol) of 4-nitrophenyl 2-[6′-(4-fluorophenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]ethylcarbamate, described in Example 4 (step 4.4.), 0.19 g (1.5 mmol) of N,N-diisopropylethylamine, 0.006 g (0.05 mmol) of N,N-dimethylaminopyridine and 0.51 g (1.1 mmol) of 2,2,2-trifluoro-1-thiazol-4-ylethanol, obtained in step 5.1., and after chromatography on silica gel, eluting with a 40/60 mixture of ethyl acetate and cyclohexane, followed by recrystallization from a mixture of diethyl ether and hexane, gives 0.240 g of pure product in the form of a white powder.

Workup

  1. customobtained in step 5.1
  2. wash, and after chromatography on silica gel, eluting with a 40/60 mixture of ethyl acetate and cyclohexane
  3. customfollowed by recrystallization from a mixture of diethyl ether and hexane

Sources & evidence

ORD record
ord-29783b006dc241d6bfc228dfca72a63f
Source dataset
uspto-grants-2014_12
Patent number
US08912218B2

Reaction notes

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