Sodium Cyanide → 3-[5-Cyano-4-[(2,2-dimethyl-propyl)-methyl-amino]-6-(4-methyl-[1,4]diazepan-1-yl)-pyrimidin-2-ylamino]-N-methoxy-4-methyl-benzamide

HRID 852048Notes

Reaction equation

HRID 852048 reaction equation
[CH3:1][C:2]([CH3:34])([CH3:33])[CH2:3][N:4]([CH3:32])[C:5]1[CH:10]=[C:9]([N:11]2[CH2:17][CH2:16][CH2:15][N:14]([CH3:18])[CH2:13][CH2:12]2)[N:8]=[C:7]([NH:19][C:20]2[CH:21]=[C:22]([CH:28]=[CH:29][C:30]=2[CH3:31])[C:23]([NH:25][O:26][CH3:27])=[O:24])[N:6]=1.[C-:35]#[N:36].[Na+].BrBr>[Na].C(=O)(O)[O-].C(Cl)Cl.O>[C:35]([C:10]1[C:5]([N:4]([CH2:3][C:2]([CH3:34])([CH3:33])[CH3:1])[CH3:32])=[N:6][C:7]([NH:19][C:20]2[CH:21]=[C:22]([CH:28]=[CH:29][C:30]=2[CH3:31])[C:23]([NH:25][O:26][CH3:27])=[O:24])=[N:8][C:9]=1[N:11]1[CH2:17][CH2:16][CH2:15][N:14]([CH3:18])[CH2:13][CH2:12]1)#[N:36]

Participants

7

Reactant 3

HCID 8929Sodium CyanideHCID 24408BromineHCID 208006343-[4-[(2,2-dimethyl-propyl)-methyl-amino]-6-(4-methyl-[1,4]diazepan-1-yl)-pyrimidin-2-ylamino]-N-methoxy-4-methyl-benzamide

Product 1

HCID 103003043-[5-Cyano-4-[(2,2-dimethyl-propyl)-methyl-amino]-6-(4-methyl-[1,4]diazepan-1-yl)-pyrimidin-2-ylamino]-N-methoxy-4-methyl-benzamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 50987224Sodium hydrogen-carbonateSolvent

Procedure

To a stirred mixture of 3-[4-[(2,2-dimethyl-propyl)-methyl-amino]-6-(4-methyl-[1,4]diazepan-1-yl)-pyrimidin-2-ylamino]-N-methoxy-4-methyl-benzamide (140 mg, 0.29 mmol) and sodium cyanide (0.044 g, 0.89 mmol) in sat. aq. sodium-bicarbonate (1 mL) and methylene chloride (3 mL) was added bromine (0.045 mL, 0.87 mmol). The resulting mixture was stirred for 16 h at room temp, then 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. C26H38N8O2 MS m/e=495 (M+H). Deprotection was performed as described in Example 75.

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-9d27c5d621424ccaa53874b3a7972ebb
Source dataset
uspto-grants-2007_08
Patent number
US07253174B2

Reaction notes

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