2-(2,6-Dichlorophenyl)acetyl isothiocyanate → N-(4-(2-(1-Methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-ylamino)phenyl carbamothioyl)-2-phenylacetamide

HRID 1711067Notes

Reaction equation

HRID 1711067 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7]1[S:15][C:14]2[C:9](=[N:10][CH:11]=[CH:12][C:13]=2[NH:16][C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=2)[CH:8]=1.Cl.Cl.N1C2C(=NC=CC=2OC2C=CC(N[C:43]([NH:45][C:46](=[O:56])[CH2:47][C:48]3[C:53](Cl)=[CH:52][CH:51]=[CH:50][C:49]=3Cl)=[S:44])=CC=2F)C=C1.ClC1C=CC=C(Cl)C=1CC(N=C=S)=O.[N-]=C=S>>[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7]1[S:15][C:14]2[C:9](=[N:10][CH:11]=[CH:12][C:13]=2[NH:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:43]([NH:45][C:46](=[O:56])[CH2:47][C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=3)=[S:44])=[CH:19][CH:18]=2)[CH:8]=1

Participants

5

Reactant 4

HCID 594244392-(2,6-Dichlorophenyl)acetyl isothiocyanateHCID 59424632N1-(2-(1-Methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yl)benzene-1,4-diamineHCID 86604194N-(4-(1H-Pyrrolo[3,2-b]pyridin-7-yloxy)-3-fluorophenylcarbamothioyl)-2-(2,6-dichlorophenyl)acetamide dihydrochlorideHCID 178418790HCID 178418790, compound

Product 1

HCID 59424511N-(4-(2-(1-Methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-ylamino)phenyl carbamothioyl)-2-phenylacetamideYield 12%

Procedure

Starting from the compound 301, following the procedures described above for the synthesis of compound 269b (scheme 61, example 222) but replacing 2-(2,6-dichlorophenyl)acetyl isothiocyanate with 2-phenylacethyl isothiocyanate, title compound 302 was obtained in 12% yield, as a yellow solid. 1H NMR (d-DMSO) δ (ppm): 12.47 (s, 1H), 11.76 (s, 1H), 10.83 (s, 1H), 8.41(d, 1H, J=6.9Hz), 7.84 (s, 1H), 7.80 (s, 1H), 7.78 (s, 1H), 7.55(s, 1H), 7.46 (s, 1H), 7.43 (s, 1H), 7.32 (m, 4H), 7.28-7.20 (m, 1H), 7.20 (s, 1H), 6.94(d, 1H, J=6.8 Hz), 3.98 (s, 3H), 3.81 (s, 2H). MS (m/z): 499.1 (M+H) (found).

Sources & evidence

ORD record
ord-15ee30e2a3f54768b431d7efd541b921
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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