1,2-Dichloroethane → tert-butyl 3-phenyl-5-(3-(pyridin-4-yl)-1-trityl-1H-indazole-5-carboxamido)piperidine-1-carboxylate

HRID 1467308Notes

Reaction equation

HRID 1467308 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:16](O)=[O:17])[CH:14]=3)[N:9]([C:19]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:8]=2)=[CH:3][CH:2]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C.[NH2:61][CH:62]1[CH2:67][CH:66]([C:68]2[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=2)[CH2:65][N:64]([C:74]([O:76][C:77]([CH3:80])([CH3:79])[CH3:78])=[O:75])[CH2:63]1>CN(C=O)C>[C:68]1([CH:66]2[CH2:67][CH:62]([NH:61][C:16]([C:13]3[CH:14]=[C:15]4[C:10](=[CH:11][CH:12]=3)[N:9]([C:19]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[N:8]=[C:7]4[C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)=[O:17])[CH2:63][N:64]([C:74]([O:76][C:77]([CH3:80])([CH3:79])[CH3:78])=[O:75])[CH2:65]2)[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 58592957Tert-butyl 3-amino-5-phenylpiperidine-1-carboxylateHCID 679963353-pyridin-4-yl-1-trityl-1H-indazole-5-carboxylic acid

Product 1

HCID 67995717tert-butyl 3-phenyl-5-(3-(pyridin-4-yl)-1-trityl-1H-indazole-5-carboxamido)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

To a microwave vial equipped with a stir bar was added 3-pyridin-4-yl-1-trityl-1H indazole-5-carboxylic acid (155.4 mg, 0.323 mmol), HOBT (74.1 mg, 0.484 mmol), EDC (93 mg, 0.484 mmol), DIPEA (225 μl, 1.291 mmol), tert-butyl 3-amino-5-phenylpiperidine-1-carboxylate (89 mg, 0.323 mmol), and DMF (3227 μl). The vial was sealed and heated to 45° C. The LCMS taken after 4 hours indicates formation of the desired product. The material was filtered through a column pre-packed with celite and was concentrated under reduced pressure. A column was run from 100% hexanes to 100% ethyl acetate. The desired product eluted and fractions were collected and concentrated in vacuo. The material was dissolved in acetonitrile and water and was dried on the lyophilizer.

Workup

  1. customTo a microwave vial equipped with a stir bar
  2. customThe vial was sealed

Sources & evidence

ORD record
ord-5ce3e67119ac48618c71320b11f1ea86
Source dataset
uspto-grants-2015_04
Patent number
US08999957B2

Reaction notes

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