4-(Dimethylsulfamoyl)benzoic acid → (4,6-Dimethyl-pyrimidin-5-yl)-(5-{2-[4-(3-fluoro-phenyl)-1-(1-trifluoromethyl-cyclopropanecarbonyl)-piperidin-4-yl]-ethyl}-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl)-methanone

HRID 1865294Notes

Reaction equation

HRID 1865294 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([N:10]2[CH2:17][CH:16]3[CH:12]([CH2:13][N:14]([CH2:18][CH2:19][C:20]4([C:26]5[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=5)[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)[CH2:15]3)[CH2:11]2)=[O:9])=[C:6]([CH3:33])[N:5]=[CH:4][N:3]=1.[F:34][C:35]([F:43])([F:42])[C:36]1([C:39](O)=[O:40])[CH2:38][CH2:37]1.CC1(C(O)=O)CC1.CNS(C1C=CC(C(O)=O)=CC=1)(=O)=O.CN(C)S(C1C=CC(C(O)=O)=CC=1)(=O)=O.S(C1C=C(C=CC=1)C(O)=O)(=O)(=O)N.CNS(C1C=C(C=CC=1)C(O)=O)(=O)=O.CN(C)S(C1C=C(C=CC=1)C(O)=O)(=O)=O.CS(NC1C=CC(C(O)=O)=CC=1)(=O)=O.CC(C)(CO)C(O)=O>>[CH3:33][C:6]1[C:7]([C:8]([N:10]2[CH2:17][CH:16]3[CH:12]([CH2:13][N:14]([CH2:18][CH2:19][C:20]4([C:26]5[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=5)[CH2:21][CH2:22][N:23]([C:39]([C:36]5([C:35]([F:43])([F:42])[F:34])[CH2:38][CH2:37]5)=[O:40])[CH2:24][CH2:25]4)[CH2:15]3)[CH2:11]2)=[O:9])=[C:2]([CH3:1])[N:3]=[CH:4][N:5]=1

Participants

11

Reactant 10

HCID 145724-(Dimethylsulfamoyl)benzoic acidHCID 785483-Hydroxy-2,2-dimethylpropionic acidHCID 813261-Methylcyclopropanecarboxylic acidHCID 2293523-Sulfamoylbenzoic acidHCID 2506534-(Methylsulfonamido)benzoic acidHCID 2526543-(Methylsulfamoyl)benzoic acidHCID 5060564-(Methylsulfamoyl)benzoic acidHCID 27783061-(Trifluoromethyl)cyclopropane-1-carboxylic acidHCID 49857623-(N,N-dimethylsulfamoyl)benzoic acidHCID 68576683(4,6-Dimethyl-pyrimidin-5-yl)-(5-{2-[4-(3-fluoro-phenyl)-piperidin-4-yl]-ethyl}-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl)-methanone

Product 1

HCID 24937670(4,6-Dimethyl-pyrimidin-5-yl)-(5-{2-[4-(3-fluoro-phenyl)-1-(1-trifluoromethyl-cyclopropanecarbonyl)-piperidin-4-yl]-ethyl}-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl)-methanone

Procedure

The following were prepared analogously from (4,6-dimethyl-pyrimidin-5-yl)-(5-{2-[4-(3-fluoro-phenyl)-piperidin-4-yl]-ethyl}-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl)-methanone using the carboxylic acid in parenthesis in place of 1-trifluoromethylcyclopropanecarboxylic acid: I-42 (1-methyl-cyclopropanecarboxylic acid), I-15 (4-methylsulfamoyl-benzoic acid), I-16 (4-dimethylsulfamoyl-benzoic acid), I-17 (3-sulfamoyl-benzoic acid), I-18 (3-methylsulfamoyl-benzoic acid), I-19 (3-dimethylsulfamoyl-benzoic acid), I-21 (4-methanesulfonylamino-benzoic acid) and I-44 (2,2-dimethyl-3-hydroxy-propionic acid).

Sources & evidence

ORD record
ord-13017b2e51c4422bafd3698600574e1f
Source dataset
uspto-grants-2009_12
Patent number
US07625905B2

Reaction notes

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