1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58703274, compound

HRID 501175Notes

Reaction equation

HRID 501175 reaction equation
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][N:2]1[CH2:14][C:15]1[S:19][C:18](/[CH:20]=[CH:21]/[C:22](O)=[O:23])=[CH:17][CH:16]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[NH2:46][O:47][CH:48]1[CH2:53][CH2:52][CH2:51][CH2:50][O:49]1>C(Cl)Cl.CCN(C(C)C)C(C)C>[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][N:2]1[CH2:14][C:15]1[S:19][C:18](/[CH:20]=[CH:21]/[C:22]([NH:46][O:47][CH:48]2[CH2:53][CH2:52][CH2:51][CH2:50][O:49]2)=[O:23])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 68461135HCID 68461135, compound

Product 1

HCID 58703274HCID 58703274, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 81531DiisopropylethylamineSolvent

Procedure

A solution of (2E)-3-[5-(1,3,4,9-tetrahydro-2H-b-carbolin-2-ylmethyl)thien-2-yl]acrylic acid in DCM (2 mL) and DIEA (0.11 mL) was sequentially treated with HOBT (32 mg), EDCI (64 mg) and NH2OTHP (40 mg). After three hours, the solvent was evaporated and the residue purified by flash chromatography on silica gel eluting with EtOAc. (2E)-3-[5-(1,3,4,9-Tetrahydro-2H-b-carbolin-2-ylmethyl)thien-2-yl]-N-(tetrahydro-2H-pyran-2-yloxy)acrylamide was obtained as a yellow oil (37 mg), m/e=438 (M+1).

Workup

  1. customthe solvent was evaporated
  2. customthe residue purified by flash chromatography on silica gel eluting with EtOAc

Sources & evidence

ORD record
ord-fda946ad4cbb411eb7eb0bcf4a49d906
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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