Isopropylamine → HCID 22638548, compound

HRID 2416221Notes

Reaction equation

HRID 2416221 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[S:8][CH:9]=[C:10]([C:12]3[C:13](=[O:24])[NH:14][C:15]4[C:20]([CH:21]=3)=[CH:19][CH:18]=[C:17]([CH:22]=O)[CH:16]=4)[N:11]=2)=[CH:3][CH:2]=1.C(OCC)(OCC)OCC.[CH:35]([NH2:38])([CH3:37])[CH3:36].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CN(C=O)C.CC(O)=O>[CH:35]([NH:38][CH2:22][C:17]1[CH:16]=[C:15]2[C:20]([CH:21]=[C:12]([C:10]3[N:11]=[C:7]([C:4]4[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=4)[S:8][CH:9]=3)[C:13](=[O:24])[NH:14]2)=[CH:19][CH:18]=1)([CH3:37])[CH3:36]

Participants

7

Reactant 4

HCID 6363IsopropylamineHCID 31214Ethyl orthoformateHCID 5049666Sodium triacetoxyborohydrideHCID 22638533HCID 22638533, compound

Product 1

HCID 22638548HCID 22638548, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(2-pyridin-4-yl-thiazol-4-yl)-1H-quinolin-2-one-7-carbaldehyde (step (a), 100 mg, 0.3 mmol), 1.5 mL AcOH, 1.5 mL of triethyl orthoformate, isopropylamine (0.5 mL), and 30 mL of DMF was stirred for 3 h. Gentle heating was be used to bring about a homogenous solution. After 3 h, NaBH(OAc)3 (0.5 g, Aldrich) was added and the reaction was stirred for 3 days at RT. The solution was concentrated in genevac overnight to remove DMF. The resulting solid was dissolved in a minimal amount of DMSO and purified by mass triggered HPLC to give a yellow solid after drying in genevac (TFA salt). MS m/z: 377.3 (M+1).

Workup

  1. temperatureGentle heating
  2. concentrationThe solution was concentrated in genevac overnight
  3. customto remove DMF
  4. dissolutionThe resulting solid was dissolved in a minimal amount of DMSO
  5. custompurified by mass
  6. customto give a yellow solid
  7. dry with materialafter drying in genevac (TFA salt)

Sources & evidence

ORD record
ord-e408b71a968f451d8bb155a00773427e
Source dataset
uspto-grants-2004_11
Patent number
US06822097B1

Reaction notes

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