Pyrrolidine → HCID 86761837, compound

HRID 2091957Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[C:16]([Cl:17])=[CH:15][N:14]=[C:13]([NH:18][C:19]2[CH:20]=[C:21]([C:37]([O:39]C)=O)[C:22]([C:27]3[CH:32]=[CH:31][C:30]([C:33](=[O:36])[NH:34][CH3:35])=[CH:29][CH:28]=3)=[CH:23][C:24]=2[O:25][CH3:26])[N:12]=1)(=[O:3])[NH2:2].[NH:41]1[CH2:45][CH2:44][CH2:43][CH2:42]1>>[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[C:16]([Cl:17])=[CH:15][N:14]=[C:13]([NH:18][C:19]2[C:24]([O:25][CH3:26])=[CH:23][C:22]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([NH:34][CH3:35])=[O:36])=[CH:29][CH:28]=3)=[C:21]([C:37]([N:41]3[CH2:45][CH2:44][CH2:43][CH2:42]3)=[O:39])[CH:20]=2)[N:12]=1)(=[O:3])[NH2:2]

Participants

Reactant 2

HCID 31268Pyrrolidine

HCID 25265267HCID 25265267, compound

Product 1

HCID 86761837HCID 86761837, compound

Conditions

Temperature: 100 °C

Procedure

The mixture of methyl 4-(4-(2-carbamoylphenylamino)-5-chloropyrimidin-2-ylamino)-5-methoxy-4′-(methylcarbamoyl)biphenyl-2-carboxylate (Step 1, 220 mg, 0.75 mmol) and 1 mL of pyrrolidine is heated at 100° C. overnight. The crude is concentrated in vacuo and applied to preparative RP-HPLC to afford 4′-(4-(2-Carbamoylphenylamino)-5-chloropyrimidin-2-ylamino)-5′-methoxy-N-methyl-2′-(pyrrolidine-1-carbonyl)biphenyl-4-carboxamide; ESMS m/z 600.2 (M+H+).

Workup

concentrationThe crude is concentrated in vacuo

Sources & evidence

ORD record: ord-976446f6b548408d8caecc8fec0399d8
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440681B2

Reaction notes

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