Diisopropylethylamine → HCID 86663978, compound

HRID 712266

Reaction equation

HRID 712266 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([C:16]#[CH:17])=[CH:14][C:13]([C:18]3[CH:19]=[N:20][C:21]([N:24]4[CH2:29][CH2:28][C:27]([CH3:35])([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:26][CH2:25]4)=[N:22][CH:23]=3)=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2].[N:36]([CH2:39][Si:40]([CH3:43])([CH3:42])[CH3:41])=[N+:37]=[N-:38].C(N(C(C)C)C(C)C)C>CN(C=O)C.O.[Cu]I>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([C:16]3[N:38]=[N:37][N:36]([CH2:39][Si:40]([CH3:43])([CH3:42])[CH3:41])[CH:17]=3)=[CH:14][C:13]([C:18]3[CH:23]=[N:22][C:21]([N:24]4[CH2:25][CH2:26][C:27]([CH3:35])([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:28][CH2:29]4)=[N:20][CH:19]=3)=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2]

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 150751Trimethylsilylmethyl AzideHCID 86663977HCID 86663977, compound

Product 1

HCID 86663978HCID 86663978, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Ethyl 1-[5-[2-(ethylcarbamoylamino)-7-ethynyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (115 mg, 0.233 mmol), (azidomethyl)trimethylsilane (150 mg, 1.169 mmol), Copper(I)Iodide (8.9 mg, 0.0467 mmol), N-ethyl-N-isopropylpropan-2-amine (30.1 mg, 0.233 mmol) in 2 mL of DMF were stirred at rt for 24 hours. The reaction was diluted with 10 mL of water, filtered and washed with water then dried to yield the desired compound as a beige solid, 95 mg, 65.5 yield %.

Workup

  1. filtrationfiltered
  2. washwashed with water
  3. customthen dried

Sources & evidence

ORD record
ord-a266206c4e3843fcad043263bbec6f89
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Linked notes

Loading…