1,2-Dichloroethane → N-[(3R)-1-(2-cyanobenzyl)piperidin-3-yl]-3-pyridin-4-yl-1-trityl-1H-indazole-5-carboxamide

HRID 1467306Notes

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][C@@H:62]1[CH2:67][CH2:66][CH2:65][N:64]([CH2:68][C:69]2[CH:76]=[CH:75][CH:74]=[CH:73][C:70]=2[C:71]#[N:72])[CH2:63]1>CN(C=O)C>[C:71]([C:70]1[CH:73]=[CH:74][CH:75]=[CH:76][C:69]=1[CH2:68][N:64]1[CH2:65][CH2:66][CH2:67][C@@H:62]([NH:61][C:16]([C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[N:9]([C:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:8]=[C:7]3[C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)=[O:17])[CH2:63]1)#[N:72]

Participants

Conditions

Temperature: 40 °C

Procedure

To a microwave vial equipped with a stir bar was added 3-(pyridin-4-yl)-1-trityl-1H-indazole-5-carboxylic acid (50 mg, 0.104 mmol), HOBT (23.85 mg, 0.156 mmol), EDC (29.9 mg, 0.156 mmol), DIPEA (54.4 μl, 0.311 mmol), 2-{[(3R)-3-aminopiperidin-1-yl]methyl}benzonitrile (22.35 mg, 0.104 mmol), and DMF (1038 μl). The vial was sealed and heated to 40° C. The LCMS taken after 23 hours indicates formation of the desired product. The crude reaction mixture was filtered through a column pre-packed with celite. The material was dry loaded onto 2×10 g columns. The desired product eluted and fractions were collected and concentrated in vacuo.

Workup

customTo a microwave vial equipped with a stir bar
customThe vial was sealed

Sources & evidence

ORD record: ord-114e80e182674399bf2e744408e4f6b5
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999957B2

Reaction notes

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