1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58392991, compound

HRID 469049Notes

Reaction equation

Cl.Cl.[CH3:3][NH:4][CH2:5][C:6]1[S:7][C:8]([CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[N:9][N:10]=1.CCN(C(C)C)C(C)C.[CH3:26][O:27][C:28]1[CH:33]=[C:32]([CH3:34])[C:31]([S:35]([N:38]([CH2:40][C:41]2[O:45][CH:44]=[C:43]([C:46]([OH:48])=O)[CH:42]=2)[CH3:39])(=[O:37])=[O:36])=[C:30]([CH3:49])[CH:29]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl>[CH3:26][O:27][C:28]1[CH:29]=[C:30]([CH3:49])[C:31]([S:35]([N:38]([CH2:40][C:41]2[O:45][CH:44]=[C:43]([C:46]([N:4]([CH3:3])[CH2:5][C:6]3[S:7][C:8]([CH2:11][N:12]4[CH2:16][CH2:15][CH2:14][CH2:13]4)=[N:9][N:10]=3)=[O:48])[CH:42]=2)[CH3:39])(=[O:36])=[O:37])=[C:32]([CH3:34])[CH:33]=1

Participants

Conditions

Temperature: 0 °C

Procedure

N-methyl-1-[5-(pyrrolidin-1-ylmethyl)-1,3,4-thiadiazol-2-yl]methanamine dihydrochloride (25 mg, 0.087 mmol) was dissolved in DCM (5 mL), on addition of DIPEA (0.03 mL, 0.17 mmol). 5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid (30 mg, 0.09 mmol) and HOBt (17 mg, 0.12 mmol) were added and the resulting solution was cooled to 0° C. prior to the addition of EDCI (24 mg, 0.13 mmol). The mixture was stirred at ambient temperature for 7 h, quenched with saturated aqueous NaHCO3 (3 mL) and extracted with DCM (2×10 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo. The residue was purified by FCC eluting with 2% MeOH in DCM to afford the title compound.

Workup

customquenched with saturated aqueous NaHCO3 (3 mL)
extractionextracted with DCM (2×10 mL)
dry with materialThe combined organic extracts were dried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by FCC
washeluting with 2% MeOH in DCM

Sources & evidence

ORD record: ord-1036079d39b94891997c57ba5fa5b4ae
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08623859B2

Reaction notes

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