Dimethylformamide → HCID 67305053, compound

HRID 1922000Notes

Reaction equation

HRID 1922000 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([NH:19][CH3:20])[N:14]=1)[CH:7]=[C:6]2[NH:21][CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.C(N(CC)C(C)C)(C)C.CN(C)C=O.[C:42](Cl)(=[O:58])[O:43][CH2:44][CH:45]1[C:57]2[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=2[C:51]2[C:46]1=[CH:47][CH:48]=[CH:49][CH:50]=2>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10]([CH:9]=[C:8]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19][CH3:20])[N:14]=3)[CH:7]=[C:6]2[NH:21][CH:22]2[CH2:27][CH2:26][N:25]([C:42]([O:43][CH2:44][CH:45]3[C:46]4[CH:47]=[CH:48][CH:49]=[CH:50][C:51]=4[C:52]4[C:57]3=[CH:56][CH:55]=[CH:54][CH:53]=4)=[O:58])[CH2:24][CH2:23]2)=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 343679-Fluorenylmethyl chloroformateHCID 81531DiisopropylethylamineHCID 58336320HCID 58336320, compound

Product 1

HCID 67305053HCID 67305053, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(6-methoxy-4-(piperidin-4-ylamino)naphthalen-2-yl)-N-methylpyrimidin-2-amine 150 (0.46 g, 1.32 mmol), N,N-diisopropylethylamine (0.92 mL, 5.2 mmol), N,N-dimethylformamide (2 mL), and tetrahydrofuran (10 mL), (9H-fluoren-9-yl)methyl carbonochloridate (0.41 g, 1.6 mmol) was added. The reaction was stirred at room temperature for 30 min and then partitioned between water (100 mL) and ethyl acetate (200 mL). The aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organics were dried over sodium sulfate, filtered and concentrated (rotary). The residue was purified by column chromatography (silica gel) using 60% ethyl acetate/hexanes as the eluent to afford (9H-fluoren-9-yl)methyl 4-((7-methoxy-3-(2-(methylamino)pyrimidin-4-yl)naphthalen-1-yl)amino)piperidine-1-carboxylate 205 as a yellow solid (0.53 g). LC/MS (m/z): 586 [M+H].

Workup

  1. custompartitioned between water (100 mL) and ethyl acetate (200 mL)
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×100 mL)
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated (rotary)
  6. customThe residue was purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-f6fee6e2256e4519b7064877f91aff28
Source dataset
uspto-grants-2012_05
Patent number
US08173808B2

Reaction notes

Loading…