Boronic Acid → tert-Butyl (5-bromo-4-cyclopropyl-1,3-thiazol-2-yl)carbamate

HRID 661101Notes

Reaction equation

HRID 661101 reaction equation
C1[C:10]2[C:5](=CC(C3SC(N)=NC=3)=CC=2)[CH:4]=CN=1.[Br:17][C:18]1[S:22][C:21]([N:23]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:24][C@@H:25]([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:26][C:27]2[CH:28]=[N:29][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:31][CH:32]=2)=[N:20][CH:19]=1.B(O)O>>[Br:17][C:18]1[S:22][C:21]([NH:23][C:45](=[O:46])[O:47][C:48]([CH3:49])([CH3:50])[CH3:51])=[N:20][C:19]=1[CH:10]1[CH2:5][CH2:4]1.[Br:17][C:18]1[S:22][C:21]([N:23]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:24][C@@H:25]([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:41])([CH3:42])[CH3:43])[CH2:26][C:27]2[CH:28]=[N:29][C:30]([C:33]([F:36])([F:34])[F:35])=[CH:31][CH:32]=2)=[N:20][CH:19]=1

Participants

5

Reactant 3

HCID 61668Boronic AcidHCID 57634141HCID 57634141, compoundHCID 86635458HCID 86635458, compound

Product 2

HCID 45117858tert-Butyl (5-bromo-4-cyclopropyl-1,3-thiazol-2-yl)carbamateHCID 57634141HCID 57634141, compound

Procedure

Example 170, N—((S)-2-amino-3-(6-trifluoromethyl)pyridine-3-yl)propyl)-5-(isoquinolin-6-yl)thiazol-2-amine: The title compound was synthesized in a manner similar to that described for Example 81 using (S)-tert-butyl 1-(5-bromothiazol-2-yl-(Boc)-amino)-3-(6-(trifluoromethyl)pyridin-3-yl)propan-2-ylcarbamate to couple with the boronic acid. (S)-tert-butyl 1-(5-bromothiazol-2-yl-(Boc)-amino)-3-(6-(trifluoromethyl)pyridin-3-yl)propan-2-ylcarbamate was synthesized as shown in Scheme 39. Theoretical (M+H) 430.4 found 430.4.

Sources & evidence

ORD record
ord-5e4915fb0d454881b8486f5e9355e377
Source dataset
uspto-grants-2011_12
Patent number
US08084479B2

Reaction notes

Loading…