1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(-3-hydroxymethyl-4-{[(3-methyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-2-phenyl-butyramide

HRID 1592703Notes

Reaction equation

HRID 1592703 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:11][N:12]([CH2:23][C:24]2[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][N:25]=2)[C@@H:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20]C=3)[CH2:16][CH2:15][CH2:14]2)=[C:7]([CH2:9][OH:10])[CH:8]=1.[C:31]1([C@H:37]([CH2:41][CH3:42])[C:38]([OH:40])=O)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.CC[N:45]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[OH:10][CH2:9][C:7]1[CH:8]=[C:3]([CH:4]=[CH:5][C:6]=1[CH2:11][N:12]([CH2:23][C:24]1[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][N:25]=1)[CH:13]1[C:22]2[N:45]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:16][CH2:15][CH2:14]1)[CH2:2][NH:1][C:38](=[O:40])[CH:37]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH2:41][CH3:42]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 785329(S)-2-Phenylbutyric acidHCID 67272335(S)-(5-aminomethyl-2-{[(3-methyl-pyridin-2-ylmethyl)-(1,2,3,4-tetrahydro-naphthalen-1-yl)amino]-methyl}-phenyl)-methanol

Product 1

HCID 67271806N-(-3-hydroxymethyl-4-{[(3-methyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-2-phenyl-butyramideYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using General Procedure G: To a solution (S)-(5-aminomethyl-2-{[(3-methyl-pyridin-2-ylmethyl)-(1,2,3,4-tetrahydro-naphthalen-1-yl)amino]-methyl}-phenyl)-methanol (128 mg, 0.32 mmol) dissolved in CH2Cl2 (10 mL) was added (S)-2-phenylbutyric acid (74 μl, 0.48 mmol), EDCI (92 mg, 0.48 mmol), HOBT (65 mg, 0.48 mmol), and DIPEA (83 μl, 0.48 mmol). Purification via column chromatography on silica gel (CH2Cl2:MeOH, 97:3, v/v) afforded COMPOUND 439 as a colorless oil (37 mg, 22%). 1H NMR (CDCl3) δ 0.86 (m, 3H), 1.44 (m, 2H), 1.81 (m, 1H), 2.18 (m, 1H), 2.23 (s, 6H), 2.64 (m, 2H), 3.22 (m, 1H), 3.85 (m, 4H), 4.14 (m, 2H), 4.31 (m, 2H), 5.73 (m, 1H), 7.14 (m, 12H), 8.36 (m, 2H); ES-MS m/z 572 (M+H).

Workup

  1. customPurification via column chromatography on silica gel (CH2Cl2

Sources & evidence

ORD record
ord-9e9cb68318e34dab923501863142725a
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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