Sodium cyanoborohydride → HCID 69591833, compound

HRID 1796000Notes

Reaction equation

HRID 1796000 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][C:8]([CH3:12])([CH3:11])[CH:9]=O)([CH3:4])([CH3:3])[CH3:2].[NH2:14][CH:15]([C:18]1[N:23]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22](=[O:31])[C:21]2=[CH:32][CH:33]=[CH:34][N:20]2[N:19]=1)[CH2:16][CH3:17].[BH3-]C#N.[Na+]>CO>[C:1]([O:5][C:6](=[O:13])[NH:7][C:8]([CH3:12])([CH3:11])[CH2:9][NH:14][CH:15]([C:18]1[N:23]([CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:22](=[O:31])[C:21]2=[CH:32][CH:33]=[CH:34][N:20]2[N:19]=1)[CH2:16][CH3:17])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 14578674tert-butyl N-(2-methyl-1-oxopropan-2-yl)carbamateHCID 221799762-(1-amino-propyl)-3-benzyl-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one

Product 1

HCID 69591833HCID 69591833, compoundYield 258%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1,1-Dimethyl-2-oxo-ethyl)-carbamic acid tert-butyl ester (88.0 mg, 0.047 mmol) and 2-(1-amino-propyl)-3-benzyl-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one (Example 26, 100 mg, 0.314 mmol) in CH3OH (20 mL) was stirred at 25° C. for 1 h and then treated with NaCNBH3 (29.5 mg, 0.47 mmol). The mixture was stirred for 0.5 h at which time a white precipitate had formed. The precipitate was collected, washed with cold CH3OH and air dried to afford the desired material (55 mg, 39%) as a white crystalline solid: 1H NMR (DMSO-d6, 400 MHz) δ 7.36 (s, 1H), 7.10 (m, 5H), 6.82 (s, 1H), 6.46 (s, 1H), 5.47 (s, 1H), 5.20 (m, 2H), 3.55 (s, 1H), 2.45 (s, 1H), 2.22 (s, 1H), 1.84 (s, 1H), 1.64 (m, 1H), 1.53 (m, 1H), 1.26 (s, 9H), 1.01 (s, 6H), 0.72 (m, 3H).

Workup

  1. customhad formed
  2. customThe precipitate was collected
  3. washwashed with cold CH3OH and air
  4. customdried

Sources & evidence

ORD record
ord-af64e1fcac9948dc8af3222af61c8405
Source dataset
uspto-grants-2006_04
Patent number
US07030118B2

Reaction notes

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