Methyl iodide → N-(4-(1-Benzyl-1H-pyrrolo[2,3-c]pyridin-7-yloxy)-3-fluorophenylcarbamothioyl)-2-phenylacetamide

HRID 1711040Notes

Reaction equation

HRID 1711040 reaction equation
ClC1N=CC=C2C=CNC=12.[F:11][C:12]1[CH:13]=[C:14]([NH:29][C:30]([NH:32][C:33](=[O:41])[CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[S:31])[CH:15]=[CH:16][C:17]=1[O:18][C:19]1[N:20]=[CH:21][CH:22]=[C:23]2[CH:27]=[CH:26][N:25]([CH3:28])[C:24]=12.C(Br)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.CI>>[CH2:28]([N:25]1[C:24]2=[C:19]([O:18][C:17]3[CH:16]=[CH:15][C:14]([NH:29][C:30]([NH:32][C:33](=[O:41])[CH2:34][C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)=[S:31])=[CH:13][C:12]=3[F:11])[N:20]=[CH:21][CH:22]=[C:23]2[CH:27]=[CH:26]1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

5

Reactant 4

HCID 6328Methyl iodideHCID 7498Benzyl BromideHCID 114350487-Chloro-1H-pyrrolo[2,3-c]pyridineHCID 86604193N-(3-Fluoro-4-(1-methyl-1H-pyrrolo[2,3-c]pyridin-7-yloxy)phenylcarbamothioyl)-2-phenylacetamide

Product 1

HCID 59424684N-(4-(1-Benzyl-1H-pyrrolo[2,3-c]pyridin-7-yloxy)-3-fluorophenylcarbamothioyl)-2-phenylacetamide

Procedure

Starting from the compound 259 and following the procedures described above for the synthesis of compound 262b (scheme 60, step 4, example 219) but using benzyl bromide in step 1 instead of methyl iodide, title compound 262c was obtained. 1H NMR (DMSO-d6) δ (ppm): 12.36 (s, 1H), 11.76 (s, 1H), 7.78 (m, 1H), 7.58(t, 1H, J1=J2=2.7 Hz), 7.50(d, 1H, J=5.7 Hz), 7.34 (m, 5H), 7.30-7.221 (m, 5H), 7.15(dd, 1H, J1=8.1 Hz, J2=0.4 Hz), 7.10(t, 1H), 6.60(d, 1H, J=2.9 Hz), 5.68 (s, 2H), 3.82 (s, 2H). MS (m/z): 511.2 (M+H) (found).

Sources & evidence

ORD record
ord-5896e42325524806b8424bb6cde4b54d
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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