3-Pyridinemethanamine → HCID 11606358, compound

HRID 2220672Notes

Reaction equation

C([O:8][C:9]([C:11]1[C:12]([C:18]2[CH:23]=[C:22]([C:24](=[O:33])[NH:25][CH2:26][C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)[CH:21]=[CH:20][C:19]=2[CH2:34][C:35]2[C:43]3[C:38](=[CH:39][C:40]([C:44]#[N:45])=[CH:41][CH:42]=3)[N:37]([CH2:46][CH3:47])[CH:36]=2)=[CH:13][CH:14]=[C:15]([CH3:17])[CH:16]=1)=[O:10])C1C=CC=CC=1.[NH2:48]CC1C=NC=CC=1>>[C:44]([C:40]1[CH:39]=[C:38]2[C:43]([C:35]([CH2:34][C:19]3[CH:20]=[CH:21][C:22]([C:24](=[O:33])[NH:25][CH2:26][C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=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:36][N:37]2[CH2:46][CH3:47])=[CH:42][CH:41]=1)(=[NH:45])[NH2:48]

Participants

Reactant 2

HCID 310183-Pyridinemethanamine

HCID 69202151HCID 69202151, compound

Product 1

HCID 11606358HCID 11606358, compoundYield 88%

Procedure

Part E. 2′-(6-cyano-1-ethyl-1H-indol-3-ylmethyl)-4-methyl-5′-[(pyridin-3-ylmethyl)-carbamoyl]-biphenyl-2-carboxylic acid benzyl ester: The compound of Part D was coupled with 3-aminomethylpyrdine using the procedure described for Example 15, Part G to provide the amide in 88% yield. 1H NMR (500 MHz, CDCl3) δ ppm 1.38 (t, J=7.42 Hz, 3H) 2.41 (s, 3H) 3.79 (s, 2H) 4.04 (q, J=7.15 Hz, 2H) 4.60 (m, 2H) 4.94 (m, 2H) 6.29 (t, J=5.50 Hz, 1H) 6.67 (s, 1H) 6.97 (d, J=7.70 Hz, 1H) 7.03 (m, 2H) 7.16 (d, J=8.25 Hz, 1H) 7.24 (m, 7H) 7.44 (s, 1H) 7.56 (s, 1H) 7.67 (t, J=8.52 Hz, 2H) 7.82 (s, 1H) 8.53 (s, 1H) 8.57 (s, 1H). LC/MS m/z 619.4 (M+H)+.

Sources & evidence

ORD record: ord-f9d35c098de54daabb728223812ab114
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07417063B2

Reaction notes

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