2-bromo-N-cyclopropyl-4-Thiazolecarboxamide → HCID 136348497, compound

HRID 634295Notes

Reaction equation

HRID 634295 reaction equation
[CH:1]([NH:4][C:5]1[O:6][C:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15](S(C2C=CC(C)=CC=2)(=O)=O)[CH:14]=[C:13]3B2OC(C)(C)C(C)(C)O2)=[N:8][N:9]=1)([CH3:3])[CH3:2].Br[C:39]1[S:40][CH:41]=[C:42]([C:44]([NH:46][CH:47]2[CH2:49][CH2:48]2)=[O:45])[N:43]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:47]1([NH:46][C:44]([C:42]2[N:43]=[C:39]([C:13]3[C:12]4[C:16](=[CH:17][CH:18]=[C:10]([C:7]5[O:6][C:5]([NH:4][CH:1]([CH3:2])[CH3:3])=[N:9][N:8]=5)[CH:11]=4)[NH:15][CH:14]=3)[S:40][CH:41]=2)=[O:45])[CH2:48][CH2:49]1

Participants

4

Reactant 2

HCID 150095472-bromo-N-cyclopropyl-4-ThiazolecarboxamideHCID 68328163HCID 68328163, compound

Product 1

HCID 136348497HCID 136348497, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

The title compound (34 mg, 30% yield) as a yellow crystalline solid was prepared according to Example 275, using N-isopropyl-5-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (145 mg, 0.278 mmol), 2-bromo-N-cyclopropylthiazole-4-carboxamide (75 mg, 0.305 mmol), and Pd(PPh3)4 (Strem Chemicals, 16 mg) as the starting materials and reagent. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.15 (1H, br.), 8.57 (1H, s), 8.29 (2H, m), 8.15 (1H, s), 7.74 (1H, d, J=7.4 Hz), 7.65 (2H, d, J=8.6 Hz), 3.77 (1H, m), 2.90 (1H, m), 1.25 (6H, d, J=6.1 Hz), 0.75 (2H, m.), 0.69 (2H, m). MS (ESI, pos. ion) m/z 409.1 (M+H)+.

Sources & evidence

ORD record
ord-9ad8758fd6b34d47a12945766dbc76d9
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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