Tert-butyl 1-(4-(2-fluoro-4-(3-(2-phenylacetyl)thioureido)phenoxy)thieno[3,2-d]pyrimidine-6-carbonyl)pyrrolidin-3-ylcarbamate → n-(4-(6-(3-Aminopyrrolidine-1-carbonyl)thieno[3,2-d]pyrimidin-4-yloxy)-3-fluorophenylcarbamothioyl)-2-phenylacetamide hydrochloride

HRID 1710977Notes

Reaction equation

HRID 1710977 reaction equation
[ClH:1].Cl.FC1C=C(NC(NC(=O)CC2C=CC=CC=2)=S)C=CC=1OC1C=CN=C2C=C(C3C=CC(N4CCNCC4)=CC=3)SC=12.[F:45][C:46]1[CH:76]=[C:75]([NH:77][C:78]([NH:80][C:81](=[O:89])[CH2:82][C:83]2[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=2)=[S:79])[CH:74]=[CH:73][C:47]=1[O:48][C:49]1[C:50]2[S:57][C:56]([C:58]([N:60]3[CH2:64][CH2:63][CH:62]([NH:65]C(=O)OC(C)(C)C)[CH2:61]3)=[O:59])=[CH:55][C:51]=2[N:52]=[CH:53][N:54]=1>>[ClH:1].[NH2:65][CH:62]1[CH2:63][CH2:64][N:60]([C:58]([C:56]2[S:57][C:50]3[C:49]([O:48][C:47]4[CH:73]=[CH:74][C:75]([NH:77][C:78]([NH:80][C:81](=[O:89])[CH2:82][C:83]5[CH:84]=[CH:85][CH:86]=[CH:87][CH:88]=5)=[S:79])=[CH:76][C:46]=4[F:45])=[N:54][CH:53]=[N:52][C:51]=3[CH:55]=2)=[O:59])[CH2:61]1

Participants

3

Reactant 2

HCID 59424627Tert-butyl 1-(4-(2-fluoro-4-(3-(2-phenylacetyl)thioureido)phenoxy)thieno[3,2-d]pyrimidine-6-carbonyl)pyrrolidin-3-ylcarbamateHCID 86604176N-(3-Fluoro-4-(2-(4-(piperazin-1-yl)phenyl)thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-phenylacetamide di-hydrochloride

Product 1

HCID 87545777n-(4-(6-(3-Aminopyrrolidine-1-carbonyl)thieno[3,2-d]pyrimidin-4-yloxy)-3-fluorophenylcarbamothioyl)-2-phenylacetamide hydrochlorideYield 40%

Procedure

Following the procedure described above for the synthesis of compound 159 (scheme 30, example 121) but substituting Boc-protected amino compound 158 for the Boc-protected amino compound 26l, title compound 191 was obtained in 40% yield. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.77 (s, 1H), 8.12 (s, 0.5H), 8.06 (s, 0.5H), 7.92(dd, J=2.4 and 12.0 Hz, 1H), 7.54(t, J=8.4 Hz, 1H), 7.48(dd, J=2.4 and 8.4 Hz, 1H), 7.36-7.31 (m, 4H), 7.30-7.25 (m, 1H), 4.2-3.80 (m, 1H), 3.08 (s, 2H), 3.80-3.50 (m, 4H), 2.10-1.98 (m, 1H), 1.82-1.64(m, 1H). LRMS (M+1) 550.6 (100%).

Sources & evidence

ORD record
ord-5ea6cb60a2224382b2211722f149fa09
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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