Potassium Carbonate → HCID 57989818, compound

HRID 239422Notes

Reaction equation

HRID 239422 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]([CH:13]([CH3:15])[CH3:14])=[N:10][C:9]=2[C:16]2[CH:17]=[C:18]([NH:22][S:23]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=3)(=[O:25])=[O:24])[CH:19]=[CH:20][CH:21]=2)[CH:5]=[CH:4][N:3]=1.[CH:33]1([NH2:36])[CH2:35][CH2:34]1.C([O-])([O-])=O.[K+].[K+]>C(O)CCC>[CH:33]1([NH:36][C:2]2[N:7]=[C:6]([C:8]3[S:12][C:11]([CH:13]([CH3:15])[CH3:14])=[N:10][C:9]=3[C:16]3[CH:17]=[C:18]([NH:22][S:23]([C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=4)(=[O:25])=[O:24])[CH:19]=[CH:20][CH:21]=3)[CH:5]=[CH:4][N:3]=2)[CH2:35][CH2:34]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69828CyclopropylamineHCID 57989926HCID 57989926, compound

Product 1

HCID 57989818HCID 57989818, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Following a procedure analogous to the procedure described in Example 1 using N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(1-methylethyl)-1,3-thiazol-4-yl]phenyl}-3-fluorobenzenesulfonamide (100 mg, 0.20 mmol) and cyclopropylamine (141 μL, 2.0 mmol) and K2CO3 (283 mg, 2.0 mmol) in 1-butanol (5 mL) the title compound was obtained as a white powder (43 mg, 0.08 mmol, 42.2% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.51 (s, 1H), 8.05 (d, J=5.0 Hz, 1H), 7.48-7.65 (m, 5H), 7.33 (t, J=7.4 Hz, 1H), 7.19-7.23 (m, 3H), 6.09 (d, J=4.7 Hz, 1H), 3.25-3.30 (m, 1H), 2.67 (bs, 1H), 1.35 (d, J=7.0 Hz, 6H), 0.63 (d, J=4.7 Hz, 2H), 0.46 (bs, 2H). MS (ESI): 510.4 [M+H]+.

Sources & evidence

ORD record
ord-f0f37bdbdf9548b1b7eed651bbefa189
Source dataset
uspto-grants-2014_02
Patent number
US08642759B2

Reaction notes

Loading…