Pyridine → HCID 56963344, compound

HRID 1037554Notes

Reaction equation

HRID 1037554 reaction equation
NC[CH2:3][N:4]([S:28]([CH3:31])(=[O:30])=[O:29])[C:5]1[C:6]([CH:25]2[CH2:27][CH2:26]2)=[CH:7][C:8]2[C:12]([CH:13]=1)=[N:11][N:10]([C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=1)[C:9]=2[C:21]([NH:23][CH3:24])=[O:22].[C@@H:32]1([C:40]([OH:42])=[O:41])[CH2:36][CH2:35][CH2:34][C@@H:33]1[C:37]([OH:39])=O.[N:43]1C=CC=[CH:45][CH:44]=1>>[Br:20][C:17]1[CH:18]=[CH:19][C:14]([N:10]2[C:9]([C:21](=[O:22])[NH:23][CH3:24])=[C:8]3[C:12]([CH:13]=[C:5]([N:4]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:3][CH2:45][CH2:44][NH:43][C:37]([C@H:33]4[CH2:34][CH2:35][CH2:36][C@H:32]4[C:40]([OH:42])=[O:41])=[O:39])[C:6]([CH:25]4[CH2:27][CH2:26]4)=[CH:7]3)=[N:11]2)=[CH:15][CH:16]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 727374cis-Cyclopentane-1,2-dicarboxylic acidHCID 569627726-[(2-aminoethyl)(methylsulfonyl)amino]-2-(4-bromophenyl)-5-cyclopropyl-N-methyl-2H-indazole-3-carboxamide

Product 1

HCID 56963344HCID 56963344, compoundYield 8%

Procedure

A mixture of Compound (7) (6.4 mg, 0.012 mmol) and cis-1,2-cyclopentanedicarboxylic acid (1.9 mg, 0.014 mmol) in pyridine (0.2 mL) was stirred at RT over the weekend. The solvent was removed under pressure. The crude material was purified by preparative LCMS (5-100% ACN in 0.1% aqueous formic acid) to afford Compound (63) as a white solid (0.7 mg, 8%). ESI-MS m/z calculated for [M+H]+: 660.2/662.2; found: 660.0/662.0; 1H NMR (400 MHz, CDCl3) δ 7.93 (s, 0.5H), 7.87 (s, 0.5H), 7.71 (d, J=8.7 Hz, 2H), 7.51 (dd, J=8.8, 2.2 Hz, 2H), 7.40 (d, J=3.7 Hz, 1H), 6.02-5.92 (m, 1H), 5.87 (d, J=4.1 Hz, 1H), 4.05-3.68 (m, 2H), 3.68-3.40 (m, 1H), 3.35-2.95 (m, 3H), 3.21 (s, 3H), 3.05 (d, J=4.9 Hz, 3H), 2.55-2.37 (m, 1H), 2.28-2.11 (m, 1H), 2.10-1.89 (m, 7H), 1.20-0.90 (m, 3H), 0.72-0.47 (m, 1H).

Workup

  1. customThe solvent was removed under pressure
  2. customThe crude material was purified by preparative LCMS (5-100% ACN in 0.1% aqueous formic acid)

Sources & evidence

ORD record
ord-195478ae02bf4948aecfdd4c476573a3
Source dataset
uspto-grants-2013_10
Patent number
US08546389B2

Reaction notes

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