Ammonia → HCID 66852927, compound

HRID 1406401Notes

Reaction equation

C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][N:18]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]3)=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:31]1[C:32](=[O:60])[N:33](COCC[Si](C)(C)C)[CH:34]=[C:35]([C:37](=[O:51])[NH:38][C:39]2[CH:40]=[N:41][N:42]([CH2:44][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[CH:43]=2)[CH:36]=1)=O)(C)(C)C.Cl.N>CO>[CH2:44]([N:42]1[CH:43]=[C:39]([NH:38][C:37]([C:35]2[CH:36]=[C:31]([C:9]3[NH:8][C:16]4[C:11]([CH:10]=3)=[CH:12][C:13]([CH2:17][N:18]3[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]3)=[CH:14][CH:15]=4)[C:32](=[O:60])[NH:33][CH:34]=2)=[O:51])[CH:40]=[N:41]1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of intermediate (4d), 2-[5-(1-benzyl-1H-pyrazol-4-ylcarbamoyl)-2-oxo-1-(2-trimethylsilanyl-ethoxymethyl)-1,2-dihydro-pyridin-3-yl]-5-(4-tert-butoxycarbonyl-piperazin-1-ylmethyl)-indole-1-carboxylic acid tert-butyl ester, 120 mg, 0.14 mmol) in methanol (4 mL) was added hydrochloric acid, 37% (0.75 mL). The mixture was heated at 90° C. for 3 hours. The reaction was allowed to attain ambient temperature and the pH adjusted to 7 by the careful addition of ammonia solution 7N in methanol. The mixture was concentrated in vacuo and the resultant crude residue was purified via preparative HPLC at pH9, to furnish the title compound as a yellow solid, 1.83 mg, 3%.

Workup

customto attain ambient temperature
concentrationThe mixture was concentrated in vacuo
customthe resultant crude residue was purified via preparative HPLC at pH9

Sources & evidence

ORD record: ord-99372d3a030c485ead7419c8641670cd
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916591B2

Reaction notes

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