Triethylamine → HCID 136347833, compound

HRID 271529Notes

Reaction equation

HRID 271529 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[O:11][C:10]([C:12]3[CH:13]=[C:14]4[C:18](=[CH:19][CH:20]=3)[C:17](=[N:21][OH:22])[CH2:16][CH2:15]4)=[C:9]([C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)[CH:8]=2)[CH2:3][CH2:2]1.Br[CH2:30][C:31]#[N:32].C(N(CC)CC)C>ClCCl.CN(C)C=O>[OH:22][N:21]=[C:17]1[C:18]2[C:14](=[CH:13][C:12]([C:10]3[O:11][C:7]([CH:4]4[CH2:3][CH2:2][N:1]([CH2:30][C:31]#[N:32])[CH2:6][CH2:5]4)=[CH:8][C:9]=3[C:23]3[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=3)=[CH:20][CH:19]=2)[CH2:15][CH2:16]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11534BromoacetonitrileHCID 136341916HCID 136341916, compound

Product 1

HCID 136347833HCID 136347833, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of the product of Example 40 Step 5 (0.13 g, 0.35 mmol) in dry dichloromethane (10 ml) and dry dimethylformamide (0.5 ml) was treated with bromoacetonitrile (0.027 ml, 0.39 mmol) and triethylamine (0.054 ml, 0.39 mmol) and stirred at ambient temperature overnight. The crude reaction mixture was poured onto an SCX column and eluted with methanol followed by a mixture of 0.880 ammonia/methanol (1:10). The basic fractions were combined, concentrated in vacuo and triturated with diethyl ether to afford the title compound (0.13 g, 90%); MS(ES+) m/e 413 [M+H]+.

Workup

  1. customThe crude reaction mixture
  2. additionwas poured onto an SCX column
  3. washeluted with methanol
  4. additionfollowed by a mixture of 0.880 ammonia/methanol (1:10)
  5. concentrationconcentrated in vacuo
  6. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-8855cc676c724d718bdd1c20a29d78cb
Source dataset
uspto-grants-2008_11
Patent number
US07452906B2

Reaction notes

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