2-(Aminomethyl)-5-methylpyrazine → HCID 11555891, compound

HRID 2220673Notes

Reaction equation

C([O:8][C:9]([C:11]1[C:12]([C:18]2[CH:23]=[C:22]([C:24](=[O:34])[NH:25][CH2:26][C:27]3[CH:32]=[N:31][C:30]([CH3:33])=[CH:29][N:28]=3)[CH:21]=[CH:20][C:19]=2[CH2:35][C:36]2[C:44]3[C:39](=[CH:40][C:41]([C:45]#[N:46])=[CH:42][CH:43]=3)[N:38]([CH2:47][CH3:48])[CH:37]=2)=[CH:13][CH:14]=[C:15]([CH3:17])[CH:16]=1)=[O:10])C1C=CC=CC=1.C(C1C=C2C(C(CC3C=CC(C(=O)NCC4C=NC=CC=4)=CC=3C3C(C(O)=O)=CC(C)=CC=3)=CN2CC)=CC=1)(=N)[NH2:50].NCC1C=NC(C)=CN=1>>[C:45]([C:41]1[CH:40]=[C:39]2[C:44]([C:36]([CH2:35][C:19]3[CH:20]=[CH:21][C:22]([C:24](=[O:34])[NH:25][CH2:26][C:27]4[CH:32]=[N:31][C:30]([CH3:33])=[CH:29][N:28]=4)=[CH:23][C:18]=3[C:12]3[C:11]([C:9]([OH:8])=[O:10])=[CH:16][C:15]([CH3:17])=[CH:14][CH:13]=3)=[CH:37][N:38]2[CH2:47][CH3:48])=[CH:43][CH:42]=1)(=[NH:50])[NH2:46]

Participants

Reactant 3

HCID 27564962-(Aminomethyl)-5-methylpyrazine

HCID 11606358HCID 11606358, compound

HCID 69201246HCID 69201246, compound

Product 1

HCID 11555891HCID 11555891, compoundYield 84%

Procedure

Part A. 2′-(6-cyano-1-ethyl-1H-indol-3-ylmethyl)-4-methyl-5′-[(5-methylpyrazin-2-ylmethyl)-carbamoyl]-biphenyl-2-carboxylic acid benzyl ester: The compound of Example 37, Part D was coupled with 2-aminomethyl-5-methylpyrazine using the procedure described for Example 15, Part G to provide the amide in 84% yield. 1H NMR (500 MHz, CDCl3) δ ppm 1.37 (t, J=7.42 Hz, 4H) 2.41 (s, 3H) 2.55 (s, 3H) 3.78 (s, 2H) 4.03 (q, J=7.51 Hz, 2H) 4.71 (dd, J=11.00, 4.95 Hz, 2H) 4.95 (m, 2H) 6.66 (s, 1H) 7.01 (m, 4H) 7.17 (dd, J=14.30, 8.25 Hz, 2H) 7.24 (m, 4H) 7.51 (s, 1H) 7.55 (s, 1H) 7.67 (d, J=8.25 Hz, 1H) 7.83 (s, 1H) 8.36 (s, 1H) 8.52 (s, 1H).

Sources & evidence

ORD record: ord-fd3795bf68174123a538a8a41da27764
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07417063B2

Reaction notes

Loading…