trans-Crotonyl chloride → HCID 78318809, compound

HRID 527410Notes

Reaction equation

FC(F)(F)C(O)=O.[NH2:8][C:9]1[CH:10]=[C:11]([N:15]2[C:20]3[N:21]=[C:22]([NH:25][C:26]4[CH:31]=[CH:30][C:29]([N:32]5[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]5)=[CH:28][C:27]=4[O:39][CH3:40])[N:23]=[CH:24][C:19]=3[CH:18]=[CH:17][C:16]2=[O:41])[CH:12]=[CH:13][CH:14]=1.[C:42](Cl)(=[O:46])/[CH:43]=[CH:44]/[CH3:45]>>[CH3:40][O:39][C:27]1[CH:28]=[C:29]([N:32]2[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]2)[CH:30]=[CH:31][C:26]=1[NH:25][C:22]1[N:23]=[CH:24][C:19]2[CH:18]=[CH:17][C:16](=[O:41])[N:15]([C:11]3[CH:10]=[C:9]([NH:8][C:42](=[O:46])/[CH:43]=[CH:44]/[CH3:45])[CH:14]=[CH:13][CH:12]=3)[C:20]=2[N:21]=1

Participants

Reactant 2

HCID 643131trans-Crotonyl chloride

HCID 86732023HCID 86732023, compound

Product 1

HCID 78318809HCID 78318809, compoundYield 14%

Procedure

This compound (10 mg, 14% yield) as a yellow amorphous solid was prepared according to the procedures described for Example 1, using 8-(3-aminophenyl)-2-((2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)amino)pyrido[2,3-d]pyrimidin-7(8H)-one 2,2,2-trifluoroacetate (1b, 78 mg, 0.14 mmol) and (E)-crotonoyl chloride (Sigma Aldrich, 0.013 mL, 0.14 mmol) as the starting materials. m/z (ESI, +ve ion) 526.3 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.17 (1H, s), 8.76 (1H, s), 8.17 (1H, br. s.), 7.92 (1H, d, J=9.4 Hz), 7.84 (1H, br. s.), 7.61 (1H, s), 7.50 (1H, t, J=8.0 Hz), 7.29 (1H, d, J=8.8 Hz), 6.99 (1H, d, J=7.6 Hz), 6.76-6.86 (1H, m), 6.54 (1H, s), 6.46 (1H, d, J=9.4 Hz), 6.14 (1H, d, J=15.1 Hz), 6.05 (1H, d, J=16.0 Hz), 3.79 (3H, s), 3.05 (4H, br. 2.45 (4H, d, J=4.5 Hz), 2.24 (3H, s), 1.85-1.91 (3H, m).

Sources & evidence

ORD record: ord-ac6eb11428754933ae1b1b4d673a5b5c
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346801B2

Reaction notes

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