Hydrochloric Acid → Hydrochloric Acid

HRID 1050618Notes

Reaction equation

HRID 1050618 reaction equation
CN(C)[C:3](=[O:32])[NH:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]2[N:12]=[C:13]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][O:30][CH3:31])=[CH:23][CH:22]=3)[C:14]([C:17]([NH2:19])=[O:18])=[N:15][CH:16]=2)[CH2:6]1.[C:34]1([C@@H:40]([NH2:42])[CH3:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(O)(C(F)(F)F)=O.[ClH:50]>CN1C(=O)CCC1.CC#N>[CH3:31][O:30][CH2:29][CH2:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([NH:20][C:13]2[C:14]([C:17]([NH2:19])=[O:18])=[N:15][CH:16]=[C:11]([N:7]3[CH2:8][CH2:9][CH2:10][C@@H:5]([NH:4][C:3]([NH:42][C@H:40]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[CH3:41])=[O:32])[CH2:6]3)[N:12]=2)=[CH:22][CH:23]=1.[ClH:50]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 758181-Phenethylamine, (-)-HCID 118114801HCID 118114801, compound

Product 2

HCID 313Hydrochloric AcidHCID 118114436HCID 118114436, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (R)-5-(3-(3,3-dimethylureido)piperidin-1-yl)-3-(4-(2-methoxyethoxyl)phenylamino)pyrazine-2-carboxamide (235) (14 mg, 0.03 mmol) in 1 mL NMP in a sealed tube added (S)-(−)-1-phenylethylamine (50 μL). The mixture was stirred in 100° C. bath for overnight. It was acidified with 0.5 mL TFA, and subjected to reverse phase preparative HPLC using 5 mM HCl (aq) and neat MeCN to isolate the title compound, 3-(4-(2-methoxyethoxyl)phenylamino)-5-((R)-3-(3-((S)-1-phenylethyl)ureido)piperidin-1-yl)pyrazine-2-carboxamide (506) as HCl salt (9.5 mg). LC-MS (ESI): m/z (M+1) 534.2. UV: λ=268, 276, 304, 339, 375 nm.

Sources & evidence

ORD record
ord-6a919b3c41864408ae40eb1e36b85527
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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