Diisopropylethylamine → HCID 89692949, compound

HRID 1481845Notes

Reaction equation

HRID 1481845 reaction equation
[CH:1]1([C:4]2[O:5][CH:6]=[C:7]([C:9]([OH:11])=O)[N:8]=2)[CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.[NH2:21][C:22]1[C:23]([N:41]2[CH2:46][CH2:45][N:44]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=3[CH3:53])[CH2:43][CH2:42]2)=[CH:24][C:25]([F:40])=[C:26]([CH:39]=1)[C:27]([NH:29][CH2:30][CH2:31][CH2:32][N:33]1[CH2:37][CH2:36][CH2:35][C:34]1=[O:38])=[O:28].[Cl-].[Li+]>CN(C=O)C>[F:40][C:25]1[C:26]([C:27](=[O:28])[NH:29][CH2:30][CH2:31][CH2:32][N:33]2[CH2:37][CH2:36][CH2:35][C:34]2=[O:38])=[CH:39][C:22]([NH:21][C:9]([C:7]2[N:8]=[C:4]([CH:1]3[CH2:2][CH2:3]3)[O:5][CH:6]=2)=[O:11])=[C:23]([N:41]2[CH2:42][CH2:43][N:44]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=3[CH3:53])[CH2:45][CH2:46]2)[CH:24]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 433294Lithium ChlorideHCID 252192732-Cyclopropyl-1,3-oxazole-4-carboxylic acidHCID 89692948HCID 89692948, compound

Product 1

HCID 89692949HCID 89692949, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2-cyclopropyl-oxazole-4-carboxylic acid 1h (22.8 mg, 0.149 mmol) in DMF (5.0 mL) HATU (75.4 mg, 0.198 mmol) was added and stirred for 3 min. N, N-diisopropylethylamine (0.086 mL, 0.496 mmol) was added to this followed by 5-amino-2-fluoro-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-4-(4-o-tolyl-piperazin-1-yl)-benzamide 3d (45.0 mg, 0.099 mmol) in DMF (2.0 mL) and the reaction was stirred at room temperature for 16 h. Saturated solution of lithium chloride was added to this and the contents were extracted with ethyl acetate dried on anhydrous sodium sulfate, concentrated and the crude 3e was dissolved in methanol and purified on preparative HPLC using water/methanol as eluent.

Workup

  1. stirringthe reaction was stirred at room temperature for 16 h
  2. extractionwere extracted with ethyl acetate
  3. dry with materialdried on anhydrous sodium sulfate
  4. concentrationconcentrated
  5. dissolutionthe crude 3e was dissolved in methanol
  6. custompurified on preparative HPLC

Sources & evidence

ORD record
ord-34a6279f2e2c4820983f40216c6df300
Source dataset
uspto-grants-2016_08
Patent number
US09409897B2

Reaction notes

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