(2-Methoxyethyl)(methyl)amine → HCID 67990229, compound

HRID 1184793Notes

Reaction equation

HRID 1184793 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH:13]2[CH2:17][C:16]3[CH:18]=[C:19]([C:22]4[CH:27]=[CH:26][C:25]([C:28]([OH:30])=O)=[CH:24][CH:23]=4)[CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[CH3:53][O:54][CH2:55][CH2:56][NH:57][CH3:58]>CN(C)C=O>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH:13]2[CH2:17][C:16]3[CH:18]=[C:19]([C:22]4[CH:27]=[CH:26][C:25]([C:28](=[O:30])[N:57]([CH2:56][CH2:55][O:54][CH3:53])[CH3:58])=[CH:24][CH:23]=4)[CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 300977(2-Methoxyethyl)(methyl)amineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67973843HCID 67973843, compound

Product 1

HCID 67990229HCID 67990229, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 4-[5-(4-carboxy-phenyl)-2,3-dihydro-benzofuran-2-yl]-piperidine-1-carboxylic acid isopropyl ester (41 mg) in N,N-dimethylformamide (1 mL) diethyl-isopropylamine (52 mL) and 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU, 32 mg) are added. After 10 min N-(2-methoxyethyl)-methylamine (12 mg) in N,N-dimethylformamide (0.5 mL) is added. The mixture is stirred for 12 h and purified by preparative HPLC (eluent water (+0.1% TFA)/MeOH) to yield the desired product. HPLC (method 12): tR=1.99 min; Mass spectrum (ESI+): m/z=481 [M+H]+.

Workup

  1. additionare added
  2. custompurified by preparative HPLC (eluent water (+0.1% TFA)/MeOH)

Sources & evidence

ORD record
ord-c970ade7d0f4402389635fe70dd9c116
Source dataset
uspto-grants-2014_03
Patent number
US08669271B2

Reaction notes

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