(2-Methoxy-phenyl)-acetyl isothiocyanate → tert-Butyl 2-(4-(7-(2-fluoro-4-(3-(2-(2-methoxyphenyl)acetyl)thioureido)phenoxy)thieno[3,2-b]pyridin-2-yl)-1H-pyrazol-1-yl)ethyl(methyl)carbamate

HRID 500833Notes

Reaction equation

HRID 500833 reaction equation
[NH2:1][C:2]1[CH:33]=[CH:32][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[CH:13]=[C:14]([C:16]4[CH:17]=[N:18][N:19]([CH2:21][CH2:22][N:23]([CH3:31])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH:20]=4)[S:15][C:8]=23)=[C:4]([F:34])[CH:3]=1.FC1C=C(NC(NC(=O)CC2C=CC=CC=2)=S)C=CC=1OC1C=CN=C2C=C(C3C=CC(S(C)(=O)=O)=CC=3)SC=12.[CH3:75][O:76][C:77]1[CH:82]=[CH:81][CH:80]=[CH:79][C:78]=1[CH2:83][C:84]([N:86]=[C:87]=[S:88])=[O:85]>>[F:34][C:4]1[CH:3]=[C:2]([NH:1][C:87]([NH:86][C:84](=[O:85])[CH2:83][C:78]2[CH:79]=[CH:80][CH:81]=[CH:82][C:77]=2[O:76][CH3:75])=[S:88])[CH:33]=[CH:32][C:5]=1[O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]2[CH:13]=[C:14]([C:16]3[CH:17]=[N:18][N:19]([CH2:21][CH2:22][N:23]([CH3:31])[C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH:20]=3)[S:15][C:8]=12

Participants

4

Reactant 3

HCID 21890860(2-Methoxy-phenyl)-acetyl isothiocyanateHCID 58772875N-(3-Fluoro-4-(2-(4-(methylsulfonyl)phenyl)thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-phenylacetamideHCID 59457747tert-Butyl 2-(4-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)-1H-pyrazol-1-yl)ethyl(methyl)carbamate

Product 1

HCID 59424686tert-Butyl 2-(4-(7-(2-fluoro-4-(3-(2-(2-methoxyphenyl)acetyl)thioureido)phenoxy)thieno[3,2-b]pyridin-2-yl)-1H-pyrazol-1-yl)ethyl(methyl)carbamateYield 90%

Procedure

Starting from the amine 182, following the procedure described above for the synthesis of compound 50 (scheme 10, example 55) but replacing 2-phenylacetyl isothiocyanate with 2-(2-methoxyphenyl)acetyl isothiocyanate, title compound 183 was obtained in 90% yield. LRMS (M+1) 691.2 (100%).

Sources & evidence

ORD record
ord-f50f92b827124a94afdef79cd1eba12b
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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