2-Pyridinecarboxaldehyde → HCID 131726607, compound

HRID 917302Notes

Reaction equation

[C:1]1([CH2:7][C@@H:8]([NH:18][C:19]([C:21]2([NH:26][C:27]([C:29]3[S:33][C:32]4[CH:34]=[CH:35][CH:36]=[CH:37][C:31]=4[CH:30]=3)=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:20])[C:9](=[O:17])[NH:10][CH:11]2CCNC[CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1C=O.[OH:46][C:47]([C:49]([F:52])([F:51])[F:50])=[O:48].C1(C[C@@H](NC(C2(NC(C3SC4C=CC=CC=4C=3)=O)CCCC2)=O)C(=O)NC2CCN(CC3C=CC=CN=3)CC2)C=CC=CC=1>>[OH:48][C:47]([C:49]([F:52])([F:51])[F:50])=[O:46].[C:1]1([CH2:7][C@@H:8]([NH:18][C:19]([C:21]2([NH:26][C:27]([C:29]3[S:33][C:32]4[CH:34]=[CH:35][CH:36]=[CH:37][C:31]=4[CH:30]=3)=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:20])[C:9](=[O:17])[NH:10][CH2:11][CH2:12][CH:41]2[CH2:40][CH2:39][NH:38][CH2:43][CH2:42]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 3

HCID 142732-Pyridinecarboxaldehyde

HCID 23625017HCID 23625017, compound

HCID 131726608HCID 131726608, compound

Product 1

HCID 131726607HCID 131726607, compound

Procedure

200 mg (0.31 mmol) of benzo[b]thiophene-2-carboxylic acid {1-[2-phenyl-1(R)-(piperidin-4-ylcarbamoyl)-ethylcarbamoyl]-cyclopentyl}-amide are used for the reaction of reductive amination with pyridine 2-carboxaldehyde (64 mg, 0.6 mmol), to yield, after purification by preparative HPLC according to the method already described in the previous Examples, the desired product benzo[b]thiophene-2-carboxylic acid {1-[2-phenyl-1(R)-(1-pyridin-2-ylmethyl-piperidin-4-ylcarbamoyl)-ethylcarbamoyl]-cyclopentyl}-amide TFA salt (120 mg, 0.16 mmol).

Workup

customto yield
customafter purification by preparative HPLC

Sources & evidence

ORD record: ord-3bfa7d8a721b4a919b973ce8acf610e4
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07273856B2

Reaction notes

Loading…