HCID 58117431, compound → HCID 66853640, compound

HRID 1406399Notes

Reaction equation

HRID 1406399 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)=[O:18])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:26]1[C:27](=[O:55])[N:28](COCC[Si](C)(C)C)[CH:29]=[C:30]([C:32](=[O:46])[NH:33][C:34]2[CH:35]=[N:36][N:37]([CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH:38]=2)[CH:31]=1)=O)(C)(C)C>CO>[CH2:39]([N:37]1[CH:38]=[C:34]([NH:33][C:32]([C:30]2[CH:31]=[C:26]([C:9]3[NH:8][C:16]4[C:11]([CH:10]=3)=[CH:12][C:13]([C:17]([N:19]3[CH2:20][CH2:21][N:22]([CH3:25])[CH2:23][CH2:24]3)=[O:18])=[CH:14][CH:15]=4)[C:27](=[O:55])[NH:28][CH:29]=2)=[O:46])[CH:35]=[N:36]1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

3

Reactant 1

HCID 58117431HCID 58117431, compound2×

Product 1

HCID 66853640HCID 66853640, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared according to the experimental used in Example 1, Step 5 with intermediate (3h), 2-[5-(1-benzyl-1H-pyrazol-4-ylcarbamoyl)-2-oxo-1-(2-trimethylsilanyl-ethoxymethyl)-1,2-dihydro-pyridin-3-yl]-5-(4-methylpiperazine-1-carbonyl)-indole-1-carboxylic acid tert-butyl ester. After the usual work up the crude product was taken up in methanol (1 mL) and loaded onto a 5 g SCX column. The column was flushed with methanol and then eluted with ammonia solution 7N in methanol. The eluent was concentrated in vacuo and the residue further purified by preparative HPLC at pH 4 to afford the title compound as a brown solid, 13 mg, 10%. LC/MS RT=1.52 Min (270 nm), m/z=536 [M+H]. Total run time 3.75 min (short pos). 1H NMR (d6 DMSO): δ 2.21 (s, 3H), 2.33 (br m, 4H), 3.53-3.56 (br m, 4H) 33 (s, 2H), 7.13 (dd, 1H), 7.31 (m, 6H), 7.53 (d, 1H), 7.61 (s, 2H), 8.10 (s, 1H), 8.14 (d, 1H), 8.58 (d, 1H), 10.31 (s, 1H), 11.72 (s, 1H), 12.5 (s, 1H).

Workup

  1. customThe title compound was prepared
  2. customThe column was flushed with methanol
  3. washeluted with ammonia solution 7N in methanol
  4. concentrationThe eluent was concentrated in vacuo
  5. customthe residue further purified by preparative HPLC at pH 4

Sources & evidence

ORD record
ord-1f037a3888bc43a6abc7fd12d4dc007d
Source dataset
uspto-grants-2014_12
Patent number
US08916591B2

Reaction notes

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