3,3-Diphenylpropylamine → 3-(5-chloro-4-(4-(methylsulfonyl)phenyl)thiazol-2-yl)-1-(3,3-diphenylpropyl)-1-(2-(tetrahydro-2H-pyran-4-yl)ethyl)urea

HRID 2190353Notes

Reaction equation

HRID 2190353 reaction equation
[Cl:1][C:2]1[S:6][C:5]([NH2:7])=[N:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=1.[C:18]1([CH:24]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:25][CH2:26][NH:27][CH2:28][CH2:29][CH:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1(C(C2C=CC=CC=2)CCN)C=CC=CC=1.BrCCC1CC[O:64][CH2:63]C1>>[Cl:1][C:2]1[S:6][C:5]([NH:7][C:63](=[O:64])[N:27]([CH2:26][CH2:25][CH:24]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:28][CH2:29][CH:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)=[N:4][C:3]=1[C:8]1[CH:9]=[CH:10][C:11]([S:14]([CH3:17])(=[O:15])=[O:16])=[CH:12][CH:13]=1.[C:18]1([CH:24]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:25][CH2:26][NH:27][CH2:28][CH2:29][CH:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 796983,3-DiphenylpropylamineHCID 226370124-(2-Bromoethyl)oxaneHCID 575863843,3-diphenyl-N-(2-(tetrahydro-2H-pyran-4-yl)ethyl)propan-1-amineHCID 866281275-Chloro-4-(4-(methylsulfonyl)phenyl)thiazol-2-amine

Product 2

HCID 575863593-(5-chloro-4-(4-(methylsulfonyl)phenyl)thiazol-2-yl)-1-(3,3-diphenylpropyl)-1-(2-(tetrahydro-2H-pyran-4-yl)ethyl)ureaHCID 575863843,3-diphenyl-N-(2-(tetrahydro-2H-pyran-4-yl)ethyl)propan-1-amine

Procedure

Compound 206 was prepared according to Method D using 5-chloro-4-(4-(methylsulfonyl)phenyl)thiazol-2-amine instead of N-(4-(2-amino-5-chlorothiazol-4-yl)phenyl)methanesulfonamide and 3,3-diphenyl-N-(2-(tetrahydro-2H-pyran-4-yl)ethyl)propan-1-amine instead of N-methyl-3,3-diphenylpropan-1-amine. 3,3-diphenyl-N-(2-(tetrahydro-2H-pyran-4-yl)ethyl)propan-1-amine was prepared according to Method C using 3,3-diphenylpropan-1-amine instead of tert-butyl 4-(2-aminoethyl)piperidine-1-carboxylate and 4-(2-bromoethyl)-tetrahydro-2H-pyran instead of 3-bromo-1,1-diphenylpropane.

Sources & evidence

ORD record
ord-a0d8a02800074f47984fdaa4a9ab8312
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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