1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 66721428, compound

HRID 1640202Notes

Reaction equation

HRID 1640202 reaction equation
COC1C=CC(CN(C)[N:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:25]=[C:24]4[C:19]([CH2:20][CH2:21][CH:22]([C:26]([OH:28])=O)[CH2:23]4)=[CH:18][CH:17]=3)=[CH:11][CH2:10]2)=CC=1.[C:32]([C:36]1[CH:37]=[C:38]([CH:40]=[CH:41][CH:42]=1)[NH2:39])([CH3:35])([CH3:34])[CH3:33].CCN=C=N[CH2:48][CH2:49][CH2:50][N:51]([CH3:53])C>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[C:32]([C:36]1[CH:37]=[C:38]([NH:39][C:26]([CH:22]2[CH2:21][CH2:20][C:19]3[C:24](=[CH:25][C:16]([O:15][C:12]4[CH:11]=[CH:10][N:9]=[C:14]([N:51]([CH2:50][C:49]5[CH:48]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=5)[CH3:53])[CH:13]=4)=[CH:17][CH:18]=3)[CH2:23]2)=[O:28])[CH:40]=[CH:41][CH:42]=1)([CH3:35])([CH3:33])[CH3:34]

Participants

7

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 793343-tert-ButylanilineHCID 66721503HCID 66721503, compound

Product 1

HCID 66721428HCID 66721428, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-({1-[(4-methoxybenzyl)(methyl)amino]pyridin-4-yl}oxy)-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (581 mg, 1.39 mmol) and 3-tert-butylaniline (228 mg, 1.53 mmol) in DCM (13 mL), was added DMAP (186 mg, 1.53 mmol) and EDCI (293 mg, 1.53 mmol). The reaction mixture was allowed to stir for 18 hr, and then diluted with EtOAc and washed with water and brine. The organic solution was dried over Na2SO4 and concentrated. The residue was purified by column to give N-(3-tert-butylphenyl)-7-({2-[(4-methoxybenzyl)(methyl)amino]pyridin-4-yl}oxy)-1,2,3,4-tetrahydronaphthalene-2-carboxamide (I-179) as a white solid (491 mg, 64.3%). 1H NMR (400 MHz, d6-DMSO; HCl salt) δ: 9.98 (s, 1H), 7.97 (d, 1H), 7.64 (dd, 1H), 7.49 (d, 1H), 7.21 (dd, 1H), 7.20 (d, 1H), 7.12 (d, 2H), 7.07 (ddd, 1H), 6.96 (d, 1H), 6.87-6.92 (m, 3H), 6.37-6.49 (m, 2H), 4.69 (s, 2H), 3.72 (s, 3H), 3.17 (s, 3H), 2.72-2.99 (m, 5H), 2.03-2.99 (m, 1H), 1.73-1.84 (m, 1H), and 1.26 (s, 9H). LCMS: (FA) ES+ 550.3, ES− 448.4.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic solution was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by column

Sources & evidence

ORD record
ord-2edbc265ab3847728271bb69406f9b9a
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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