4-Methylmorpholine → HCID 56848566, compound

HRID 1470342Notes

Reaction equation

HRID 1470342 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]2[O:19][C:18]3[C:13](=[N:14][CH:15]=[CH:16][C:17]=3[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:12]=2)[CH:10]=1)[C:5](O)=[O:6].Cl.CN(C)CCCN=C=NCC.CN1CCOCC1.[NH2:45][C:46]([CH3:50])([CH3:49])[CH2:47][OH:48]>CN(C)C=O.O>[OH:48][CH2:47][C:46]([NH:45][C:5](=[O:6])[C:4]1[CH:8]=[C:9]([C:11]2[O:19][C:18]3[C:13](=[N:14][CH:15]=[CH:16][C:17]=3[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:12]=2)[CH:10]=[C:2]([CH3:1])[CH:3]=1)([CH3:50])[CH3:49]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 118072-Amino-2-methyl-1-propanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66778978HCID 66778978, compound

Product 1

HCID 56848566HCID 56848566, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

3-Methyl-5-(7-phenyl-furo[3,2-b]pyridin-2-yl)-benzoic acid (79 μmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimidhydrochlorid (86,592 μmol) are dissolved in N,N-dimethylformamid (300.00 μl) and 4-methylmorpholin (157.354 μmol) and 1-hydroxybenzotriazolhydrat (86.849 μmol) are added and stirred 5 min at RT. A solution of 2-amino-2-methyl-propan-1-ol (80,000 μmol) in N,N-dimethylformamid (100.00 μl) is added. The mixture is stirred 4.5 h at RT. The reaction solution is poured into water and extracted with ethylacetate. The combined organic layers are dried over MgSO4 and the solvent is removed in vacuo. The product is isolated after reversed phase column chromatography as yellow solid (33 μmol, 42% yield). HPLC (method A): Rt 2.55 min (purity 98.5%); LCMS (ESI+) (method E): Rt 2.199 min, M+H+401.1 m/z; 1H NMR (500 MHz, DMSO-d6) δ [ppm] 8.60 (d, J=5.1, 1H), 8.18 (s, 1H), 8.16-8.10 (m, 2H), 7.96 (s, 1H), 7.77 (s, 1H), 7.70 (d, J=8.9, 2H), 7.65 (dd, J=14.7, 6.4, 3H), 7.58 (d, J=7.4, 1H), 4.16 (br, 1H), 3.54 (s, 2H), 2.47 (s, 3H), 1.35 (s, 6H).

Workup

  1. stirringThe mixture is stirred 4.5 h at RT
  2. extractionextracted with ethylacetate
  3. dry with materialThe combined organic layers are dried over MgSO4
  4. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-aa5e00a369754f06a093588d765f54d1
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

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