HCID 59457670, compound → N-(4-(2-(1-Acetyl-1,2,3,6-tetrahydropyridin-4-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenylcarbamothioyl)-2-phenylacetamide

HRID 1711098Notes

Reaction equation

HRID 1711098 reaction equation
[NH2:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[CH:13]=[C:14]([C:16]4[CH2:21][CH2:20][N:19]([C:22](=[O:24])[CH3:23])[CH2:18][CH:17]=4)[S:15][C:8]=23)=[C:4]([F:27])[CH:3]=1.C(N1C2C(OC3C=CC(N[C:47]([NH:49][C:50](=[O:58])[CH2:51][C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)=[S:48])=CC=3F)=NC=NC=2C=C1)C>>[C:22]([N:19]1[CH2:20][CH:21]=[C:16]([C:14]2[S:15][C:8]3[C:9](=[N:10][CH:11]=[CH:12][C:7]=3[O:6][C:5]3[CH:25]=[CH:26][C:2]([NH:1][C:47]([NH:49][C:50](=[O:58])[CH2:51][C:52]4[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=4)=[S:48])=[CH:3][C:4]=3[F:27])[CH:13]=2)[CH2:17][CH2:18]1)(=[O:24])[CH3:23]

Participants

3

Reactant 2

HCID 59457670HCID 59457670, compoundHCID 866096611-(4-(5-Ethyl-5H-pyrrolo[3,2-d]pyrimidin-4-yloxy)-3-fluorophenyl)-3-(2-phenylacetyl)thiourea

Product 1

HCID 16718406N-(4-(2-(1-Acetyl-1,2,3,6-tetrahydropyridin-4-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenylcarbamothioyl)-2-phenylacetamideYield 70%

Procedure

Starting from compound 391 and following the procedure described for compound 31b (Scheme 5, step 4, example 28); title compound 385 was obtained in 70% yield. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 12.45 (s, 1H), 11.83 (s, 1H), 8.49 (dd, J=5.5 Hz, J=0.8 Hz, 1H), 8.00 (d, J=11.9 Hz, 1H), 7.58-7.49 (m, 3H), 7.41-7.35 (m, 2H), 7.21-7.13 (m, 2H), 6.65 (dd, J=5.5, 1 Hz, 1H), 6.50 (m, 1H), 4.2 (m, 1H), 4.15 (m, 1H), 3.83 (s, 2H), 3.70-3.67 (m, 2H), 2.68 (m, 1H), 2.59 (m, 1H), 2.09 (s, 1.5H), 2.04 (s, 1.5H). LCMS: 579.2 (M+H).

Sources & evidence

ORD record
ord-089fea72754c4d0c84eef0fe452f8443
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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