1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 69375332, compound

HRID 860990Notes

Reaction equation

HRID 860990 reaction equation
[CH3:1][S:2]([C:5]([C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:18]3[CH:19]=[C:20]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]=[CH:31][C:32](O)=[O:33])[CH:25]=4)[CH:21]=[CH:22][CH:23]=3)[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([CH3:7])[CH3:6])(=[O:4])=[O:3].CCN=C=N[CH2:40][CH2:41][CH2:42][N:43](C)C.C1(N)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl.[NH4+].[Cl-]>[CH:42]1([NH:43][C:32](=[O:33])[CH:31]=[CH:30][C:26]2[CH:25]=[C:24]([C:20]3[CH:21]=[CH:22][CH:23]=[C:18]([C:16]4[CH:17]=[C:8]([C:5]([S:2]([CH3:1])(=[O:4])=[O:3])([CH3:7])[CH3:6])[CH:9]=[C:10]5[C:15]=4[N:14]=[CH:13][CH:12]=[CH:11]5)[CH:19]=3)[CH:29]=[CH:28][CH:27]=2)[CH2:40][CH2:41]1

Participants

7

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 69373271HCID 69373271, compound

Product 1

HCID 69375332HCID 69375332, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A mixture of 3-{3′-[6-(1-methanesulfonyl-1-methyl-ethyl)quinolin-8-yl]-biphenyl-3-yl}-acrylic acid from Step 2 (1.0 eq.), EDCI (1.3 eq.), DMAP (2.0 eq.) and cyclopropylamine (10.0 eq.) in CH2Cl2 was stirred for 12 h at rt. The mixture was poured in saturated aqueous NH4Cl and extracted with EtOAc (2×). The combined organic extracts were washed with saturated aqueous NaHCO3, brine, dried over Na2SO4, filtered and concentrated. Flash chromatography (EtOAc) afforded the title compound as a white solid. 1H NMR (500 MHz, acetone-d6): δ 8.94 (dd, 1H), 8.46 (dd, 1H), 8.30 (d, 1H), 8.24 (d, 1H), 8.06 (s, 1H), 7.91 (s, 1H), 7.76–7.50 (m, 7H), 7.48 (t, 1H), 7.39 (d, NH), 6.7 (d, 1H), 2.87 (m, 1H), 2.75 (s, 3H), 2.02 (s, 6H), 0.71 (m, 2H), 0.52 (m, 2H).

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic extracts were washed with saturated aqueous NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-adfcfe24c68f4ac8b111b3e7d594c45d
Source dataset
uspto-grants-2006_12
Patent number
US07153968B2

Reaction notes

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