Cyanogen Bromide → HCID 86686155, compound

HRID 1409707Notes

Reaction equation

HRID 1409707 reaction equation
[CH:1]1([N:4]([CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[C:5]([C:7]2[CH:8]=[N:9][C:10]([N:13]3[CH:17]=[CH:16][N:15]=[C:14]3[CH3:18])=[N:11][CH:12]=2)=[O:6])[CH2:3][CH2:2]1.C[CH2:26][N:27](C(C)C)C(C)C.C(Br)#N>C(Cl)Cl.C1COCC1>[C:26]([N:22]1[CH2:23][CH2:24][CH:19]([N:4]([CH:1]2[CH2:3][CH2:2]2)[C:5]([C:7]2[CH:12]=[N:11][C:10]([N:13]3[CH:17]=[CH:16][N:15]=[C:14]3[CH3:18])=[N:9][CH:8]=2)=[O:6])[CH2:20][CH2:21]1)#[N:27]

Participants

6

Reactant 3

HCID 10476Cyanogen BromideHCID 81531DiisopropylethylamineHCID 710937562-(2-Methyl-imidazol-1-yl)-pyrimidine-5-carboxylic acid cyclopropyl-piperidin-4-yl-amide2×

Product 1

HCID 86686155HCID 86686155, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 2-(2-methyl-imidazol-1-yl)-pyrimidine-5-carboxylic acid cyclopropyl-piperidin-4-yl-amide (310 mg, Intermediate 20) and DIPEA (0.42 mL) in CH2Cl2 (10 mL) and THF (10 mL) is added bromocyane (120 mg) and the mixture is stirred at room temperature for 12 h. The mixture is concentrated, ethyl acetate and water are added, the organic layer is dried (MgSO4) and concentrated to yield the title compound. LC (method 3): tR=1.07 min; Mass spectrum (ESI+): m/z=352 [M+H]+.

Workup

  1. concentrationThe mixture is concentrated
  2. additionethyl acetate and water are added
  3. dry with materialthe organic layer is dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-abbe121621304dfa904ca5679f2b6b6e
Source dataset
uspto-grants-2014_12
Patent number
US08921398B2

Reaction notes

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