Diisopropylethylamine → 5-[2-(Pyridin-3-ylamino)-pyrimidin-4-yl]-thiophene-2-carboxylic acid (2-cyanoethyl)-ethyl amide
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]2[N:13]=[C:12]([C:14]3[S:18][C:17]([C:19]([OH:21])=O)=[CH:16][CH:15]=3)[CH:11]=[CH:10][N:9]=2)[CH:2]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:55]([NH:57][CH2:58][CH2:59][C:60]#[N:61])[CH3:56]>CC(N(C)C)=O>[C:60]([CH2:59][CH2:58][N:57]([CH2:55][CH3:56])[C:19]([C:17]1[S:18][C:14]([C:12]2[CH:11]=[CH:10][N:9]=[C:8]([NH:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[N:13]=2)=[CH:15][CH:16]=1)=[O:21])#[N:61]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Combined 5-[2-(Pyridin-3-ylamino)-pyrimidin-4-yl]-thiophene-2-carboxylic acid (22 mg, 0.065 mmol), DIEA (27 uL, 0.195 mmol), and HATU (36.8 mg, 0.097 mmol) in DMA (0.5 mL) in a Smith microwave vial. Added 3-ethylamino propionitrile (10.9 uL, 0.097 mmol) and heated in microwave for 900 seconds at 90° C. The crude mixture was purified by prep LCMS to afford title compound (2.7 mg, 10.9%). MS: m/z 379 (M+H+). 1H NMR (500 MHz, DMSO-d6) δ1.203 (br t, 3H), 2.88 (br t, J=6.5 Hz, 2H), 3.65 (Br s, 2H), 3.70 (Br s, 2H), 7.33 (dd, J=5, 8.5 Hz, 1H), 7.469 (dd, J=1.5, 6.5 Hz, 1H), 7.497 (dd, J=1.5, 4 Hz, 1H), 7.985 (dd, J=1.5, 4 Hz, 1H), 8.16 (m, 1H), 8.22 (m, 1H), 8.56 (dd, J=1.5, 5 Hz, 1H), 8.95 (d, J=2.5 Hz, 1H), 9.91, (s, 1H).
Workup
- customThe crude mixture was purified by prep LCMS
Sources & evidence
- ORD record
- ord-2cdf83fecc3243ca98019d346aea9f28
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07803806B2
Reaction notes
Loading…