Methylamine → HCID 54689925, compound

HRID 1244141Notes

Reaction equation

HRID 1244141 reaction equation
[Cl:1][C:2]1[S:14][C:5]2[NH:6][C:7](=[O:13])[C:8]([C:11]#[N:12])=[C:9]([OH:10])[C:4]=2[C:3]=1[C:15]1[CH:25]=[CH:24][C:18]([O:19][CH2:20][C:21]([OH:23])=O)=[CH:17][CH:16]=1.C[CH2:27][N:28]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.CN>CN(C=O)C.ClCCl>[Cl:1][C:2]1[S:14][C:5]2[NH:6][C:7](=[O:13])[C:8]([C:11]#[N:12])=[C:9]([OH:10])[C:4]=2[C:3]=1[C:15]1[CH:16]=[CH:17][C:18]([O:19][CH2:20][C:21]([NH:28][CH3:27])=[O:23])=[CH:24][CH:25]=1

Participants

8

Reactant 5

HCID 6329MethylamineHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 54689864HCID 54689864, compound

Product 1

HCID 54689925HCID 54689925, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [4-(2-chloro-5-cyano-4-hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b]pyridin-3-yl)-phenoxy]-acetic acid (20 mg, 0.053 mmol, Example 184A)), EDCI (10.2 mg, 0.053 mmol), HOBT (7.2 mg, 0.053 mmol), and NMM (0.0146 mL, 0.133 mmol), in DMF (0.4 mL) was added methylamine (0.0265 mL, 0.053 mmol, 2M in THF). The solution was stirred at room temperature overnight. The solution was diluted with dichloromethane, washed with water, concentrated to dryness and purified by RP-HPLC to give the title compound. MS (ESI) m/e 387.9 (M−H)+; 1H NMR (300 MHz, MeOD-d4) δ 2.9 (s, 3H), 4.55 (s, 2H), 4.8 (m, 2H), 6.95 (d, 2H), 7.30 (d, 2H).

Workup

  1. washwashed with water
  2. concentrationconcentrated to dryness
  3. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-ded3e20e209a4b818296bd44e9892589
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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