Melanin-concentrating hormone → n-{4-[2-{3-[(1e)-Hex-1-en-1-yl]phenyl}-2-(1h-indol-3-yl)-1-methylethyl]benzoyl}-beta-alanine

HRID 2246894Notes

Reaction equation

HRID 2246894 reaction equation
[CH:1](/[C:7]1[CH:8]=[C:9]([CH:13]([C:31]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[NH:33][CH:32]=2)[CH:14]([C:16]2[CH:30]=[CH:29][C:19]([C:20]([NH:22][CH2:23][CH2:24][C:25]([O:27]C)=[O:26])=[O:21])=[CH:18][CH:17]=2)[CH3:15])[CH:10]=[CH:11][CH:12]=1)=[CH:2]\[CH2:3][CH2:4][CH2:5][CH3:6].CC(C1NC(=O)C(CCSC)NC(=O)C(NC(C(NC(C(NC(C(NC(C(N)CC(O)=O)=O)C(O)C)=O)CCSC)=O)CCCNC(N)=N)=O)CSSCC(C(NC(C(NC(C(NC(C(O)=O)C(C)C)=O)CCC(O)=O)=O)CC2C3C(=CC=CC=3)NC=2)=O)NC(=O)C2N(CCC2)C(=O)C(CCCNC(N)=N)NC(=O)C(CC2C=CC(O)=CC=2)NC(=O)C(C(C)C)NC(=O)C(CCCNC(N)=N)NC(=O)CNC1=O)C>>[CH:1](/[C:7]1[CH:8]=[C:9]([CH:13]([C:31]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[NH:33][CH:32]=2)[CH:14]([C:16]2[CH:30]=[CH:29][C:19]([C:20]([NH:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[O:21])=[CH:18][CH:17]=2)[CH3:15])[CH:10]=[CH:11][CH:12]=1)=[CH:2]\[CH2:3][CH2:4][CH2:5][CH3:6]

Participants

3

Reactant 2

HCID 16167454Melanin-concentrating hormoneHCID 67262869Methyl n-{4-[2-{3-[(1e)-hex-1-en-1-yl]phenyl}-2-(1h-indol-3-yl)-1-methylethyl]benzoyl}-beta-alaninate

Product 1

HCID 46240594n-{4-[2-{3-[(1e)-Hex-1-en-1-yl]phenyl}-2-(1h-indol-3-yl)-1-methylethyl]benzoyl}-beta-alanine

Procedure

The title compound was prepared from the intermediate from Step A using the hydrolysis conditions described in INTERMEDIATE 2, Step G. The crude material was purified by HPLC. 1H NMR (500 MHz, CD3CN): δ 8.97 (s, 1H); 7.55 (d, J=8.3 Hz, 2H); 7.52 (d, J=7.9 Hz, 1H); 7.49 (s, 1H); 7.43 (d, J=8.3 Hz, 2H); 7.33 (d, J=7.5 Hz, 1H); 7.20 (t, J=7.6 Hz, 2H); 7.14 (m, 2H); 7.07 (broad s, 1H); 6.99-6.96 (m, 1H); 6.92-6.89 (m, 1H); 6.40-6.25 (m, 2H); 4.50 (d, J=11.5 Hz, 1H); 3.77-3.69 (m, 1H); 3.49 (q, J=6.4 Hz, 2H); 2.53 (dd, J=14.4, 21.1 Hz, 26H); 1.47-1.33 (m, 4H); 1.08 (d, J=6.8 Hz, 3H); 0.92 (t, J=7.2 Hz, 3H). LC1 3.72 min. (M+1)=509.

Workup

  1. customthe hydrolysis conditions
  2. customThe crude material was purified by HPLC
  3. customLC1 3.72 min. (M+1)=509

Sources & evidence

ORD record
ord-7fde4888b27744048013c3ea58a0c75d
Source dataset
uspto-grants-2010_03
Patent number
US07687534B2

Reaction notes

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