1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 46175902, compound

HRID 469077Notes

Reaction equation

HRID 469077 reaction equation
[CH:1]1([N:4]([CH2:18][C:19]2[O:20][CH:21]=[C:22]([C:24](O)=[O:25])[N:23]=2)[S:5]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH3:16])=[CH:10][C:9]=2[CH3:17])(=[O:7])=[O:6])[CH2:3][CH2:2]1.CCN=C=NCCCN(C)C.C1C=C2N=NN(O)C2=CC=1.O.CCN(C(C)C)C(C)C.[CH3:58][NH:59][CH:60]1[CH2:65][CH2:64][CH2:63][CH:62]([N:66]2[CH2:71][CH2:70][N:69]([CH3:72])[CH2:68][CH2:67]2)[CH2:61]1>CN(C=O)C>[CH:1]1([N:4]([CH2:18][C:19]2[O:20][CH:21]=[C:22]([C:24]([N:59]([CH3:58])[CH:60]3[CH2:65][CH2:64][CH2:63][CH:62]([N:66]4[CH2:67][CH2:68][N:69]([CH3:72])[CH2:70][CH2:71]4)[CH2:61]3)=[O:25])[N:23]=2)[S:5]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH3:16])=[CH:10][C:9]=2[CH3:17])(=[O:7])=[O:6])[CH2:2][CH2:3]1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 583930982-({Cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)-1,3-oxazole-4-carboxylic acidHCID 59449243HCID 59449243, compound

Product 1

HCID 46175902HCID 46175902, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to general procedure AH using 2-({cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)-1,3-oxazole-4-carboxylic acid (50 mg, 0.13 mmol), EDCI (50 mg, 0.26 mmol), HOBt monohydrate (40 mg, 0.26 mmol), DIPEA (90 μL, 0.52 mmol), N-methyl-3-(4-methylpiperazin-1-yl)cyclohexanamine (27 mg, 0.13 mmol) and DMF (1 mL). The resulting crude compound was purified by FCC eluting with 99:1 DCM:7N NH3 in MeOH followed by purification using prep method D.

Workup

  1. customThe resulting crude compound was purified by FCC
  2. washeluting with 99:1 DCM
  3. custom7N NH3 in MeOH followed by purification

Sources & evidence

ORD record
ord-66580bd49dc44d3e9bf899cb96700895
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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