1-(4-(2-(Dimethylcarbamoyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-3-(2-phenylacetyl)thiourea → N-(3-Fluoro-4-(6-(pyrrolidine-1-carbonyl)thieno[2,3-d]pyrimidin-4-yloxy)phenylcarbamothioyl)-2-phenylacetamide

HRID 1710991Notes

Reaction equation

HRID 1710991 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][C:7]2[C:8]3[CH:15]=[C:14]([C:16]([N:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)=[O:17])[S:13][C:9]=3[N:10]=[CH:11][N:12]=2)=[C:4]([F:25])[CH:3]=1.CN(C)C(C1SC2C(=NC=CC=2OC2C=CC(N[C:47]([NH:49][C:50](=[O:58])[CH2:51][C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)=[S:48])=CC=2F)C=1)=O>>[F:25][C:4]1[CH:3]=[C:2]([NH:1][C:47]([NH:49][C:50](=[O:58])[CH2:51][C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=2)=[S:48])[CH:24]=[CH:23][C:5]=1[O:6][C:7]1[C:8]2[CH:15]=[C:14]([C:16]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[O:17])[S:13][C:9]=2[N:10]=[CH:11][N:12]=1

Participants

3

Reactant 2

HCID 115407241-(4-(2-(Dimethylcarbamoyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-3-(2-phenylacetyl)thioureaHCID 59424640(4-(4-Amino-2-fluorophenoxy)thieno[2,3-d]pyrimidin-6-yl)(pyrrolidin-1-yl)methanone

Product 1

HCID 59424601N-(3-Fluoro-4-(6-(pyrrolidine-1-carbonyl)thieno[2,3-d]pyrimidin-4-yloxy)phenylcarbamothioyl)-2-phenylacetamideYield 17%

Procedure

Starting from the compound 210 and following the procedures described above for the synthesis of compound 8a (scheme 1, step 7, example 1), crude title compound 211 was obtained. It was purified by flash chromatography, eluents DCM and DCM-MeOH-Et3N (97.75:2:0.25) followed by trituration with a mixture of MeOH-EtOAc, to afford title compound 211 in 17% yield as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ(ppm): 12.43 (s, 1H), 11.80 (s, 1H), 8.70 (s, 1H), 8.06 (s, 1H), 7.93 (d, 1H, J=11.7/2.3 Hz), 7.53-7.47 (m, 2H), 7.34-7.26 (m, 5H), 3.90 (t, 2H, J=6.7 Hz), 3.83 (s, 2H), 3.55 (t, 2H, J=6.7 Hz), 1.99-1.85 (m, 4H). LRMS (M+1) 536.2 (100%).

Workup

  1. customcrude title compound 211 was obtained
  2. customIt was purified by flash chromatography, eluents DCM and DCM-MeOH-Et3N (97.75:2:0.25)
  3. additionfollowed by trituration with a mixture of MeOH-EtOAc

Sources & evidence

ORD record
ord-e5a5e5aa84484ac683defa4aac671b64
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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