Sodium Cyanide → HCID 10229243, compound

HRID 852049Notes

Reaction equation

HRID 852049 reaction equation
[CH3:1][C:2]([CH3:35])([CH3:34])[CH2:3][N:4]([CH3:33])[C:5]1[N:10]=[C:9]([NH:11][C:12]2[CH:13]=[C:14]([CH:21]=[CH:22][C:23]=2[CH3:24])[C:15]([NH:17][O:18][CH2:19][CH3:20])=[O:16])[CH:8]=[C:7]([N:25]2[CH2:31][CH2:30][CH2:29][N:28]([CH3:32])[CH2:27][CH2:26]2)[N:6]=1.[C-:36]#[N:37].[Na+].BrBr>C(=O)(O)[O-].[Na+].C(Cl)Cl.O>[C:36]([C:8]1[C:9]([NH:11][C:12]2[CH:13]=[C:14]([CH:21]=[CH:22][C:23]=2[CH3:24])[C:15]([NH:17][O:18][CH2:19][CH3:20])=[O:16])=[N:10][C:5]([N:4]([CH2:3][C:2]([CH3:34])([CH3:1])[CH3:35])[CH3:33])=[N:6][C:7]=1[N:25]1[CH2:31][CH2:30][CH2:29][N:28]([CH3:32])[CH2:27][CH2:26]1)#[N:37]

Participants

7

Reactant 3

HCID 8929Sodium CyanideHCID 24408BromineHCID 20800625HCID 20800625, compound

Product 1

HCID 10229243HCID 10229243, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred mixture of 3-[2-[(2,2-dimethyl-propyl)-methyl-amino]-6-(4-methyl-[1,4]diazepan-1-yl)-pyrimidin-4-ylamino]-N-ethoxy-4-methyl-benzamide (50 mg, 0.1 mmol) and sodium cyanide (0.044 g, 0.89 mmol) in sat. aq. sodium bicarbonate (1 mL) and methylene chloride (3 mL) was added at room temp bromine (0.045 mL, 0.87 mmol). The resulting mixture was continued stirring for 16 h at room temp. The reaction mixture was diluted with water and extracted with methylene chloride (2×15 mL). The combined organic layer was dried (sodium sulfate), filtered and concentrated under reduced pressure, and the product was purified by HPLC. C27H40N8O2 MS m/e=509 (M+H).

Workup

  1. extractionextracted with methylene chloride (2×15 mL)
  2. dry with materialThe combined organic layer was dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customthe product was purified by HPLC

Sources & evidence

ORD record
ord-bd60ae27ba9147f2ac5af4fad5325732
Source dataset
uspto-grants-2007_08
Patent number
US07253174B2

Reaction notes

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