Acetic Acid → HCID 69591864, compound

HRID 1795949Notes

Reaction equation

HRID 1795949 reaction equation
[NH2:1][CH:2]([C:5]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9](=[O:18])[C:8]2=[CH:19][CH:20]=[C:21]([Cl:22])[N:7]2[N:6]=1)[CH2:3][CH3:4].[C:23]([NH:30][CH:31]([CH3:34])C=O)([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].[CH3:35]C(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO>[C:26]([O:25][C:23](=[O:24])[NH:30][CH2:31][CH2:34][CH2:35][NH:1][CH:2]([C:5]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9](=[O:18])[C:8]2=[CH:19][CH:20]=[C:21]([Cl:22])[N:7]2[N:6]=1)[CH2:3][CH3:4])([CH3:27])([CH3:28])[CH3:29]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 545705tert-butyl N-(1-oxopropan-2-yl)carbamateHCID 5049666Sodium triacetoxyborohydrideHCID 86759979HCID 86759979, compound

Product 1

HCID 69591864HCID 69591864, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (±)-2-(1-aminopropyl)-3-benzyl-7-chloro-3-H-pyrrolo[2,1-f][1,2,4]triazine-4-one (0.45 g, 1.42 mmol), N-BOC-aminopropanal (J. Med. Chem., 1985, 28, 317–323, 2.36 g, 13.6 mmol) and HOAc (0.2 mL) in MeOH (12 mL) was treated with NaBH(OAc)3 (1.5 g, 6.7 mmol) and stirred at rt overnight. The reaction mixture was quenched with saturated NaHCO3 solution, extracted with EtOAc (3×80 mL). The EtOAc solution was dried over MgSO4 and concentrated to an oil. Purification of the crude product by flash column chromatography (SiO2, EtOAc/Hexane 3.5:6.5 to 3:2) gave the title compound as a pale oil (0.52 g, 77.6%): MS (ESI+) 474.24, 474.26 (M++H).

Workup

  1. customThe reaction mixture was quenched with saturated NaHCO3 solution
  2. extractionextracted with EtOAc (3×80 mL)
  3. dry with materialThe EtOAc solution was dried over MgSO4
  4. concentrationconcentrated to an oil
  5. customPurification of the crude product by flash column chromatography (SiO2, EtOAc/Hexane 3.5:6.5 to 3:2)

Sources & evidence

ORD record
ord-561f1e435c0948039292c6e0d5149976
Source dataset
uspto-grants-2006_04
Patent number
US07030118B2

Reaction notes

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