2-Bromothiazole → N-((2S,3S,E)-2-amino-3-(4-(trifluoromethyl)phenyl)hex-4-enyl)-5-(isoquinolin-6-yl)thiazol-2-amine

HRID 2109757Notes

Reaction equation

HRID 2109757 reaction equation
S(N1CC1)(C1C=CC([N+]([O-])=O)=CC=1)(=O)=O.[NH2:16][C@@H:17]([C@H:20]([C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=1)/[CH:21]=[CH:22]/[CH3:23])[CH2:18][NH2:19].Br[C:35]1[S:36][CH:37]=[CH:38][N:39]=1.[CH:40]1[C:49]2[C:44](=[CH:45][C:46](B(O)O)=[CH:47][CH:48]=2)[CH:43]=[CH:42][N:41]=1.N[C@@H]([C@H](C1C=CC(C(F)(F)F)=CC=1)/C=C/C)CO>>[NH2:16][C@@H:17]([C@H:20]([C:24]1[CH:25]=[CH:26][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:28][CH:29]=1)/[CH:21]=[CH:22]/[CH3:23])[CH2:18][NH:19][C:35]1[S:36][C:37]([C:46]2[CH:45]=[C:44]3[C:49](=[CH:48][CH:47]=2)[CH:40]=[N:41][CH:42]=[CH:43]3)=[CH:38][N:39]=1

Participants

6

Reactant 5

HCID 764302-BromothiazoleHCID 148462Aziridine, 1-((4-nitrophenyl)sulfonyl)-HCID 44119669(Isoquinolin-6-yl)boronic acidHCID 57634111(2S,3S,E)-2-amino-3-(4-(trifluoromethyl)phenyl)hex-4-en-1-olHCID 68995389(2S,3S,E)-2-amino-3-(4-(trifluoromethyl)phenyl)hex-4-enylamine

Product 1

HCID 57634013N-((2S,3S,E)-2-amino-3-(4-(trifluoromethyl)phenyl)hex-4-enyl)-5-(isoquinolin-6-yl)thiazol-2-amine

Procedure

The title compound was synthesized in a manner similar to that described for Example 35 using a nosyl aziridine intermediate to introduce the (2S,3S,E)-2-amino-3-(4-(trifluoromethyl)phenyl)hex-4-enylamine side chain to make the bromothiazole intermediate that was coupled with isoquinolin-6-ylboronic acid. The nosyl aziridne was prepared in a similar manner to that described for Example 17 starting with (2S,3S,E)-2-amino-3-(4-(trifluoromethyl)phenyl)hex-4-en-1-ol which was prepared as shown in Scheme 35. MS m/z: 469 (M+1). 1H NMR (400 MHz, CD3OD) δ ppm 9.12 (s, 1H) 8.38 (d, J=5.87 Hz, 1H) 8.03 (d, J=8.80 Hz, 1H) 7.86 (dd, J=8.61, 1.76 Hz, 1H) 7.70-7.80 (m, 2H) 7.65 (t, J=4.01 Hz, 3H) 7.50 (d, J=8.22 Hz, 2H) 5.63-5.83 (m, 2H) 3.65 (dd, J=13.11, 2.74 Hz, 1H) 3.37-3.44 (m, 2H) 3.21-3.30 (m, 1H) 1.73 (dd, J=6.26, 1.37 Hz, 3H).

Workup

  1. customwas prepared

Sources & evidence

ORD record
ord-57418d6303d44ab8885483bd8e2b60eb
Source dataset
uspto-grants-2009_04
Patent number
US07514566B2

Reaction notes

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